This never appealed to me. I’ve always been more of a creator socialist, excited when the group around me thrives, and not just a select few super-participators. I also have always sense that there must be a better way to architect digital communities in ways that make it easier for the members to connect with each other, especially in ways that don’t even require them to participate publicly. And for the first time, I think the possibilities to do this in fun ways are better than ever.

I’ll share what I’m doing but first, let’s backtrack a second.

Community 1.0

I started a community using the Circle platform in 2023 after dozens of people kept asking me if there was a place where they could find other people on pathless paths. I looked at other options like memberful, mighty networks, and Podia, but chose Circle because the costs were relatively low and I could host my courses there too.

But from the beginning, I struggled to be energized about it. Circle was solid but it didn’t quite do what I wanted it to do. This is no fault of Circles. It exists in a broader VC-funded ecosystem of a “creator economy” that needs to serve customers while increasing revenues, and eventually, profits. Over time, all of the incentives and narratives have coalesced around creator businesses, helping single creators make a lot of money and build businesses.

But building a creator empire has never been the most interesting thing to me. I don’t want to be a billion dollar creator. Hell, nor do I want to be a million dollar creator. I simply want to create, connect with others, explore ideas, and hopefully keep funding my ability to do it all. The reason I wanted to setup a community is because people wanted it.

Alas, Circle has to build a business and pay employees and return investor money. And importantly, it can’t focus on people like me who don’t think about scaling their business and maximizing monetization all the time. And so at the end of last year, as I was mostly breaking even on the community, I attempted to go in and change some of the email workflows and take advantage of some new AI features. I was hit with aggressive upsells.

This was incredibly frustrating. I felt like I already wasn’t doing a good job with my community and that if I wanted to be able to build the things I wanted to, I would first need to pay a lot more money to Circle. Luckily with the improvement in agentic coding tools, I knew I might be able to roll my own platform, something I wrote about a couple of weeks ago in my rewilding the stack essay.

So that’s exactly what I’ve done. And the core of the new platform is all built around one simple idea:

In other words, the group doesn’t need many more people to increase the value of the community, it only needs more varieties of possible edges between community members.

Edge #1: Easy ways to plant flags (literally)

Many of the people in the pathless community travel for events, host online events, and want to meet people IRL in various places around the world. I wanted to make that easier.

Step one was getting people to tag where they are in the world (the boat are those marked nomadic).

And/or share travel plans and events:

Step two, once we have this information is doing a few things:

• Having a high value weekly email with relevant notifications (more below)

• Investing in targeted local IRL events and hopefully building up bigger capacity for a larger event next year

Over the past few years there have been many random meetups that have happened around the world, something with me knowing and sometimes without me knowing. The feedback from people is that they usually want to meet more people. I love hearing about these connections and so I wanted to try to make more of them happen.

Edge #2: Curiosity Conversations

My community has always featured people sharing “curiosity conversation” links, or open call links where people can connect without an agenda. But until now, it was one-off posts lost to ephemeral feeds in WhatsApp and Circle.

Now I have a dedicated page and so far 14 people are open to chatting:

Every week, people get a highlight of who added a link and what they might want to talk about.

Edge #3: Slow posting social optimized for conversation

I don’t mind posting in public in 2026 but for many people, it is not a good experience and not something that I wanted to do. Inspired by Craig Mod’s local social media called “the good place,” I wanted to create my own mini social feed, and so I have spun up something called Field Notes.

There are two rules:

1. You can post once a week, but it has to be minimum 300 characters

2. You are allowed to reply infinite times

So far its been pretty good. People seem to like it. The goal is really to have a place where people can share deeper ideas and thoughts and have nuanced conversations without worrying about the blowback of wider social media.

Serendipity Emails: The thing tying it all together. a high-value weekly digest

Email really is the killer app and using AI tools, you can create something that’s pretty magical. I now have a workflow that:

• Captures all relevant new information, links, calls, locations, and new members and shares that each week

• Creates a draft I can review and add personalized information and an intro

• Ships it with automatic login links that are easy to use

The goal here is to create something that triggers people’s curiosity and has them saying “ooh I want to open this.”

It’s not going to be AI summaries, it’s literally just going to be what people are doing, what they are sharing, and who they might want to connect with.

Finally, flexible payments

I’m never quite sure how to charge for things. I personally love one-time payments but they are also not great for sustainability.

So I decided to just offer two models: Annual or one-time. I suspect many will choose one-time payments and that’s fine. The good thing is that I now have a platform that is cheap to run (total costs are about $5/month now) and even easier to maintain, so I don’t need it to be a big financial business like I felt it needed to be when on Circle.

Check it out here

Future thoughts on “community”

As you can tell, I’m very excited about all of this. The things I can do that weren’t possible twelve months ago are borderline magical for someone like me who’s been hacking away online for decades.

If community 1.0 on the internet has mostly been about monetizing attention to the creators benefit, I hope that this is part of a community 2.0 movement where value can spread to the entire group much more easily. In the past that required A LOT of energy from the creator, like what has built with The Lab. But with AI tools, you can spin up all sorts of things that are delightful for users and participants that never made sense financially for any company to build or offer.

And beyond that kind of value I am thinking a lot about financial value too. What does it look like to build and share squad wealth? How do we maximize the digital GDP of the broader pathless community and not just my own pocket? What are the opportunities that we are not yet thinking about that tools like Stripe + agentic coding tools unlock?

I’ve always been motivated by bringing others along, rooting for them, and then trying to connect and support as many people as possible. Most of this kind of effort is not valuable in an economic sense. But at least now I can build my own platform around this and align my energy such that the odds of stumbling into a financially viable part of my business are much higher.

And I think that’s pretty cool.

Check out the community here

Many are very upset at any attempts to write with AI and I am fine if people wish to unsubscribe. However, I think avoiding trying to write with AI is a mistake. Its an interesting and weird technology and I suspect we’ll find new ways of writing that are distinctive and interesting. We aren’t there yet though and many people hate any sort of attempt at writing with AI. I think this is a mistake and what many are mad at is new tech, lack of care put into posts, solid writing without interestingness, Writers(TM) being triggered by non-writers now deeming themselves “writers,” cheating in school, and many many more grievances.

If you don’t want to receive these, I created an AI writing section which you can unsubscribe from but I’m also cool if you unsubscribe broadly. As always, I will follow my curiosity and likely will do more co-writing with Claude but will always tag it as such. And also, I never look at who is subscribing and unsubscribing from my newsie.

The Boomer Blockade, Six Years Later

An update to the original January 2020 post, using Federal Reserve Distributional Financial Accounts data through Q4 2025 and the 2025 Crist Kolder Volatility Report. Full web version linked here.

When I wrote The Boomer Blockade in January 2020, my hot take-away was that the best predictor of becoming a CEO of a Fortune 500 company was being a baby boomer. The Crist Kolder data that inspired the piece showed the average birth year of newly appointed CEOs hadn’t budged from Boomer territory since 2005.

Six years later, that’s no longer true.

Average birth year of appointed CEO, 2010–2025

In 2010 the average appointed CEO was born in 1960 — solidly Boomer. The line drifted upward through the 2010s, sitting on the Boomer/Gen X boundary for most of the decade. In 2023 it crossed into Gen X for the first time. By 2025 it was 1967.

The best predictor of becoming a CEO is no longer being a Boomer. As of 2023, it’s being Gen X.

Congrats to Gen X. The Boomer blockade is over.

Or is it? Let’s dig in.

The Silent Generation controlled nearly 80% of wealth at the end of the 1980s, but the Boomer generation rode a wealth boom into older age

In the original post I showed a chart from Federal Reserve data on wealth adjusted for median generation age. It showed the Silent generation’s share of household wealth shrinking sharply starting in their 50s while the boomer share kept growing as the median member of the cohort was entering their 60s.

Here’s what I wrote at the time

If you compare the boomers to the silent generations, the silent generation’s share of wealth shrunk 26% from a median cohort age of 54 to 63 years old. During the same comparable period, the baby boomers increased their share of wealth by 5%. The baby boomers are growing their share of the pie into their sixties.

I went back to the Fed’s Distributional Financial Accounts and pulled all the data through Q4 2025.

When I first looked at the data in 2019, the boomers had already plateaued but I couldn’t quite predict how it would evolve. It turns out that it had already started declining, with the peak being late 2016 at 57.6%.

Six years later, the millennial and gen X cohorts are the ones gaining share of wealth:

Share of US household wealth by median cohort age

Part of this is that the Boomer population has shrunk and another part is that many are shifting into retirement (especially a big bump during the pandemic).

Overall the boomer share has fallen from 57.6% to 51% over nine years. Silent share keeps dropping too. But if we look at the cohorts, most of what Boomers and Silent lost went to Millennials, who climbed from 4% to 11%. Gen X barely moved, 25% to 26%.

Gen X at a median age of 52 holds 26% of household wealth. In terms of nominal gains, it was a huge increase, but if you are comparing to the dominance the Boomers had at the same age, they are only half of the Boomers 50% of share.

The big story from 1989-2025 was that the Boomers captured the majority of the new wealth created.

Who captured new wealth, 1989–2025

Part of this is that the Boomers were just bigger than every other generation. Another part is that their careers and lives coincided with a reshaping of the financial reality of American adults. Starting with the Boomers, the limits on wealth expansion in old age no longer seem to apply.

The bigger question...are the Millennials and Gen X left behind?

Turns out it’s complicated.

Gen X and Millennials are doing just as well as Boomers, but you have to adjust for inflation and cohort size

Total wealth has expanded at an unprecedented pace over the past fifteen years.

Similar to the above chart, the Boomers really were the first generation to see wealth continue to increase as they approached retirement.

Total household net worth by median cohort age

As we can see, Boomers as a generation have amassed $89.7 trillion at a median cohort age of 70. The Silent generation never broke $30T.

The obvious challenge here is that a 1989 dollar is worth far more than a 2025 dollar. So let’s adjust the same chart for real 2025 dollars.

Every cohort’s wealth at every age converted to today’s purchasing power using CPI-U:

Total household net worth by median cohort age (real 2025 dollars)

With these we see Gen X still “losing” to the Boomers and the Silent generations slide being a bit more dramatic.

But wait, you say. What about cohort size? Aren’t the Boomers a massive cohort?

Yes, good call.

I pulled population and you can see that the population sizes have shifted over time with the Millennials actually continuing to grow over time, too, because of immigration.

While Boomers were the largest cohort for most of this window, Millennials passed them around 2018. Gen X stayed smaller than both. Silent shrank as people passed away.

US population by generation, 1989–2025

Now dividing wealth by that cohort size:

Per-capita household net worth by median cohort age (real 2025 dollars)

This gives us a more coherent picture of what’s going on:

• The Boomers are behind where the Silent generation was at mid-life, but unlike the Silent generation, their wealth continued to rise in their 60s and 70s. In 1989 the Silent generation held roughly 80% of US household wealth despite being only ~17% of the US population (42.4M out of 246.8M Americans). For comparison, Boomers in 2025 hold 51% of US household wealth at ~20% of the population (66.6M out of ~340M) — a similar population share, but a much less extreme wealth concentration (~2.6x over-indexed vs Silent’s ~4.7x in 1989). That 1989 Silent concentration produced about $1.0M per capita at median age 52 — more than Boomers had at the same age in 2007 ($648K per capita), even after adjusting for inflation, because the Boomer cohort was nearly twice as large (77.9M people sharing a similar pool of wealth). What’s distinctive about Boomers is what happened after 60: per-capita wealth kept climbing to $1.35M at age 70 today, vs $1.15M the Silent generation held at 70 in 2007. Silent plateaued. Boomers didn’t.

• Gen X at 52 have much less share than what Boomers had, but adjusted for inflation and cohort size, they are ahead of Boomers. Per capita in 2025 dollars, Gen X at 52 holds $718K ($46.2T ÷ 64.4M people). Boomers at the same age in 2007 held $648K ($50.5T real ÷ 77.9M). Silent at 52 in 1989 held $1,006K ($42.7T real ÷ 42.4M — the Silent cohort was barely half the size of Boomers, so the same pool of wealth concentrated into fewer people). Gen X is ~10% ahead of where Boomers were at 52, and both are well below where Silent was at the same age once you account for the smaller Silent cohort.

• Millennials at 35 are well ahead of everyone. Per capita in 2025 dollars, Millennials at 35 hold $256K. Boomers at 35 (in 1990) held $136K. Gen X at 35 (in 2008, mid-financial-crisis) held $93K. Millennials are roughly 1.9x ahead of Boomers and 2.8x ahead of Gen X at the same age. This is an underrated trend (see Nick Maggiulli on this for a similar take).

I think the biggest takeaway is under-discussed:

The Boomer generation is the first financialized generation. It’s very clear that something shifted in the economy in terms of wealth accumulation with the boomer generation. I suspect a big contributor to this is shift away from defined pension plans and the rise of equity investing like 401ks as opposed to defined pension plans. With this shift, the Boomers are the first ones who truly are a native capitalist generation from early age until old age.

Perhaps it also explains this other chart I’ve shared in the past:

The boomers have captured the biggest share of all wealth expansion since 1990 but that has shrunk over time

Even though half of their generation is likely retired, the Boomer generation still captured the largest share of new wealth in the last ten years:

Who captured new wealth, 2015–2025

Boomers captured nearly half, despite many hitting retirement. Gen X picked up another third.

It wasn’t always this distributed. Here are the same charts for the three prior decades, drawn on the same x-axis scale so the dollar magnitudes are comparable:

Who captured new wealth, 1990–2020

Three things stand out.

First the big one: Boomers have captured the largest share of wealth for the last 35 years. Again, we know from the Silent generation data that this was not happening because the Boomers were already out-wealthing them in 1990. This is a permanent shift in how the economy works and distributes wealth to people. The rich get richer, but more broadly, every generation is getting richer too.

Second, The boomers dominated the early 2000s but capture has slowed from 61% → 86% → 52% → 46%. In the 2000s boomers captured almost every new dollar created in the entire economy, because the Silent generation was losing wealth and Gen X and Millennials hadn’t accumulated enough to register. Only in the last fifteen years did the pattern broaden, and even then boomers still got more than anyone else.

Finally, Gen X’s has caught up, their share doubled each decade. From 11% in the 1990s to 18% in the 2000s to 41% in the 2010s. Despite this, they are still second to the Boomers in terms of capturing new wealth despite its oldest cohort members approaching retirement.

In 2025, Millennials are still behind the Silent Generation in terms of total wealth and people older than 62 have nearly two thirds of all wealth

This is often the view you see shared online. Obviously there is some nuance to this as we just covered, but the most striking thing is that nearly two-thirds of all wealth is controlled by people aged 62 and older.

Total household net worth by generation, over time

I suspect a lot of anger comes from the combination of a few things:

• The Boomers probably have the most Financialized view of life

• This view has been passed down to their offspring

• People see older people controlling congress, institutions, and organizations and also know they have all the money too

• This makes people upset

While the Silent generation controlled substantial wealth later in life, they were actually capturing less of a share of the wealth than their children (the boomers) in their 50s and 60s.

Despite this, someone shared the following graphic with me from the 80s:

I guess old people complaining about young people and young people complaining about older people is a timeless tradition.

Zooming out, the trends I shared in the original Boomer blockade piece still stand

The 2020 post talked about three ideas.

1. Career disruption: Slower growth, less stable economy

2. Pseudo career paths: First generation staying longer in the workforce meant average ages for executive roles increased

3. Wealth Capture: New with Boomers = capturing the most wealth - still true

Here’s a quick accounting on the most recent data::

A couple themes that I think are driving some of the discontent toward older generations despite the fact that overall wealth seems somewhat okay:

• The career blockade is ending. But there is still a lot of frustration with housing. The CEO line crossed into Gen X in 2023. The youngest Boomer turns 62 this year, the oldest 80. Housing went the other way. The median first-time buyer is now 40 (or 33 per CFPB, both records), up from 29 in 1981. House prices ran 5x median household income in 2025, up from 3.5x in 1985. Boomer homeownership at age 27 was 40.5%; today’s under-30s are at 32.6%. Half of US renters now spend more than 30% of their income on rent — the highest reading the Harvard Joint Center for Housing Studies has ever recorded.

• The promised wealth transfer arrives after the years it was supposed to help. Cerulli now projects $124 trillion will move from Boomers to heirs and charities between 2024 and 2048, up from their 2020 estimate of $84T. The median American receives an inheritance around age 51, and closer to 60 once a surviving spouse holds it first. Many young people who are getting help, are getting lump sums to help with down payments on housing at 25 to 35 or Kids’ college tuition at 45 to 55. However, many Boomers didn’t get help themselves and don’t see that they should be helping their kids either.

Challenging my own data

I asked Claude to critique my article with real data. Here are the caveats and nuance is flagged:

Cohort size matters — see the per-capita chart above. This is the biggest qualifier on the rest of the post. The DFA reports wealth by generation as a share or total, not per capita. Boomers number 66.6 million in 2025 (down from ~78 million at their late-1990s peak). Gen X is 64.4 million. Millennials are 73.1 million. Silent is just 14.7 million now (down from ~42 million in 1989). Source: Census Bureau Population Estimates, summed by single year of age.

Same-age per-capita comparisons (real 2025 dollars):

• At age 52: Silent $1,006K (1989) · Boomer $648K (2007) · Gen X $718K (2025)

• At age 35: Boomer $136K (1990) · Gen X $93K (2008) · Millennial $256K (2025)

• At age 70: Silent $1,150K (2007) · Boomer $1,346K (2025)

Two things change once you account for cohort size:

First, Silent at 52 had more per-capita wealth than Boomers at 52 — about $1.0M vs $650K. Silent is a smaller cohort (about half the size of Boomers at the comparable life stage), so spreading their wealth across fewer people produces a higher per-person figure. The original 2020 framing of Boomers being uniquely wealth-rich in middle age doesn’t survive the per-capita check perfectly but the Boomers wealth-building in later years is new.

Second, Gen X at 52 is roughly 10% ahead of Boomers at 52 in per-capita real terms. And Millennials at 35 are nearly 2x Boomers at 35.

The real Boomer phenomenon shows up at 70: $1.35M per capita, slightly ahead of Silent’s $1.15M at the same age. That’s the gap that holds up after every correction. The middle-career story doesn’t.

Wealth is concentrated inside each cohort, too. The top 10% of any generation holds most of that generation’s wealth. The “average Boomer with $1.25M” doesn’t exist. Median Boomer net worth is closer to $400K. Same caveat for Gen X and Millennials. Generational comparisons hide bigger gaps within each cohort.

The CEO chart stitches two methodologies. 2010-2014 comes from the 2021 Crist Kolder Volatility Report; 2015-2025 from the 2025 edition. The small step at 2014→2015 reflects a sample-definition change between editions, not a real demographic shift.

Housing data spreads wide. NAR’s 2025 first-time-buyer age is 40 (a record). The CFPB’s National Mortgage Database shows 32-33 (also a record, smaller increase). Both are real. NAR’s number reflects a smaller sample of survey respondents; CFPB’s reflects mortgage originations. The direction is the same; the magnitude is contested.

Generation boundaries are not consensus. I’m using the Fed’s definitions throughout: Silent 1928-1945, Boomer 1946-1964, Gen X 1965-1980, Millennial 1981-1996. Pew agrees. The Census Bureau uses slightly different boundaries. Shifting boundaries by a few years moves all the cohort numbers around.

Sources: Federal Reserve Distributional Financial Accounts, Q4 1989 – Q4 2025, for all wealth charts. Crist Kolder Volatility Report, 2025 edition, for the CEO chart. Wealth charts use Q4 readings; cohort positioning uses the midpoint of each generation’s birth-year range. The original 2020 post lives at pmillerd.com/the-boomer-blockade.

We have no plans to go anywhere for a while :-)

Depending on who you are, this might sound awesome, or it might sound slightly insane. I welcome all judgments here on the Pathless newsletter, but thought I should at least attempt to jot down some reflections — both for my own sensemaking, and your bemusement.

#1 We had planned to move back to Asia for a while

We definitely enjoyed living in the US over the last three years, especially in Austin, but just felt increasingly pulled back to Taiwan as our daughter started speaking Chinese.

We faced some challenges with the second pregnancy, and because of that, we decided to travel around a bit longer before settling back in Taiwan. So for the last year-plus, we spent one month in Mexico, three months in the US, five months in Thailand, coming back to Taiwan for three months for my Taiwan book launch events and for Angie to finish her book, and then heading out again with 20 other families as part of the traveling village in Vietnam, Taiwan, and then Korea from January to May.

As that was ending, we signed a lease for a mountainside apartment in Taipei, where we’ll be settling for a bit, awaiting the arrival of our second daughter in July.

Someone asked if we are “settled down for good,” and I didn’t quite know how to answer. We are settled for now, and may be here for a few years, but at least for us, the concept of being settled isn’t a worry or goal. It’s actually nice knowing we could be in many locations and figure out a setup that works for us.

#2 Long-term travel is definitely a skill, and you need to rebuild some of those skills when you travel with kids

Having lived in so many places with Angie, we’ve developed a lot of interesting “hacks” to help us be quite satisfied living almost anywhere. This includes minimum travel periods (1 month), budgeting for upgrades in the first few days, and the general capacity to handle things going wrong that comes with, well, things going wrong.

With our daughter, we’ve had to develop even more skills like finding play options for her, finding formula, diapers, and childcare on the go, strategic boarding and flying strategies, and adjusting to different food availability. For the most part, although travel days can be a bit more stressful, traveling with our daughter has not been that hard. In fact, she’s injected quite a bit of joy into going to new places because she gets so excited about new apartments, new places, and trains. We’ve stuck to a pretty regular rhythm of sleep that seems to be the most important thing when having young kids. When she sleeps well, we sleep well, and when we have a rough day, we remind ourselves that we’d be facing the same challenges no matter where we lived.

I’d say the hardest time to fly was the period between 13 months and 17 months because she had just started to walk, but could not understand that you can’t crawl down the aisle during takeoff, and had zero attention span to be distracted by an iPad or literally anything. Outside of that, it was a bit stressful but generally not too bad. Out of fiftyish flights over the past few years, I think we might have had 1-2 rough ones.

#3 The challenges of traveling with a young kid are just the challenges of parenting anywhere

Wherever you go, there you are, as they say.

The biggest challenge with traveling with our daughter was that we continued to take on most of the childcare ourselves, and this just got a bit harder as she got older. One of our best setups was finding a part-time nanny while in Oaxaca for the month. In Koh Samui, we tested out something that was a little more social, as she hadn’t spent much time interacting with others. It was awesome on paper, and she loved the teachers, but she kept asking us to get rid of the other kids from the school.

This led to a change of location and also inspired my father-in-law to offer to join us in Chiang Mai to help watch our daughter through most of the second half of last year. This period was pretty magical, and he seemed to be enjoying spending time with her after retiring from his office job, though I think he was starting to hit his limits toward the end, too. Angie and I got a bit more time to connect, we found a small group of friends in Chiang Mai that we hope to spend time with again, and we both had more time to work on various projects, especially giving Angie the space to finish the final draft of her book.

At the beginning of the year, we headed to Vietnam to start the traveling village…

#4 The traveling village was awesome, but also challenging, and a lot of that was just the unique demands of our specific daughter being about three

I am so glad we did the traveling village, and with a little time to think over the past few weeks, I’ve been able to put the experience into perspective a bit more.

The positives:

• Being around families while traveling who face the weird challenges of living a nomadic life with kids was inspiring and gave us lots to think about

• For me, being around many dads who valued spending lots of time with their kids felt great. In Austin, spending 2-3 days a week with my daughter felt a bit lonely and weird. On this trip, with almost all the other dads being incredibly involved (if not the lead parent), I felt much more at home. Many of the fellow dads are in a downshift or break from work to focus on family over the next few years. It was very inspiring and reminded me that not everyone is career-maxxing.

• For Angie, being around many moms balancing motherhood, creative work, and personal time was energizing and rewarding in the same ways

• Our daughter connected really well with a couple of the twelve-year-olds on the trip who babysat a number of times throughout the trip, and it was the best “it takes a village” experience.

• As I reflect on the trip, I realize that the busyness of the trip made it hard to really digest all the really cool experiences we had as a family. I suspect this experience will have many memory dividends in the future.

• Kamal, one of the dads on the trip, threw these amazing birthday parties, including one for me, where we played basketball, I got to DJ, and also hung out with all the dads. I’ll always remember my 41st birthday, one of my favorite ones in a long time. These dads’ nights out were a highlight: There’s something special about hanging out with fellow dads putting their family first. Although we were from many different countries with all sorts of different energies, we shared a strong common bond, and I loved the feeling of shared respect in the group.

Also, some challenges:

• Our daughter has always been a bit on the shy side (see “get rid of the other kids” above), and so the large group meetups (a “nest” four days per week) were a bit tough. I would be excited to be around the other parents, but I couldn’t quite hang out with them because my daughter would either want to go home or want to play only with me. Toward the end, I found a better balance of doing things with smaller groups and/or staying home from the daytime group hangs.

• Angie was going through her book launch, and I was also still doing a bit of work throughout the trip, especially with a project in Taiwan, and we were stretched way too thin during the 2nd stop in Taiwan.

• We were a bit shy about opting into more childcare because so many on the trip were devoting almost all their time to their kids, either via planned sabbaticals, being temporarily retired, being FIRE, or having one parent handle childcare during the week. But the system Angie and I had that “worked” for the first two years fell apart as the demands of a three-year-old taxed both of our systems a bit too much while we tried to slot in random work sessions throughout the week.

Reflections/what I’d do differently

• It was amazing seeing the older kids thrive on this trip. It seems that kids aged 6-11 really loved being on this trip and would basically play with other kids non-stop when they met up. These parents had a lot more freedom to do other things or even do things with their kids. Ages five and under, I think the value of the “village” is harder to capture, and most of the work still falls on the parents. It did make me optimistic for trying something like this down the road, but I think we’d wait a few years. I’d probably also take a proper sabbatical, not just a kind of not-working but still doing stuff sabbatical.

• I’d spend more time doing smaller one-off dinners with families and helping the kids connect much earlier, and I’d likely try to set up a more structured arrangement for help within the village for our daughter.

• I’d do whatever I needed to do to find a consistent writing routine. I didn’t take this seriously enough. Lesson learned.

Overall, I’m really happy we went on the trip. It expanded my imagination for what I thought was possible, helped us find some new limits, and revealed some preferences. Mostly, I’m excited to cross paths with many of our new friends across the world in the future!

#5 We decreased our cost of living, and that feels nice

I try not to make decisions based on cost and have a principle that I live where I want to live and worry about the finances later. Despite this, it was very nice being outside of the US, where it felt like costs were accelerating on everything, and even though many people were doing financially well, everyone always seemed upset about how things were going.

The two big things that have been cheaper are housing and healthcare. Last year, we spent 45% less on housing, and this year, our housing costs will be about 30% lower. Even though Taipei is one of the most expensive cities to own property in the world, renting is still reasonable. On top of that, healthcare is essentially free in Taiwan, and they keep passing more and more subsidies for having children, driven by Taiwan being the fastest-growing country economically while having the lowest birth rate in the world. Certainly an interesting place to be.

Our current setup of housing, healthcare, and childcare is about 30-40% of what it would cost in the US, so that feels like a really nice thing to have as we have another kid and will continue to want some optionality to buy freedom.

#6 I found the lower limit of work I’d like to do

Since finishing Good Work in September 2024, I’ve had nothing close to a regular work practice or writing practice. My work days and time have been sporadic and random. I’ve probably averaged about 10-15 hours of focused work per week, with a couple of small stretches where it was closer to 25-30. I was living out the “leave money on the table” chapter in real time.

When I zoom all the way out, I’m happy with the trades I’ve made. I’m mostly trading opportunity and work satisfaction for family time. But over the past year, I’ve found myself a bit too fried and disconnected from myself after sucking it up and opting into more and more childcare. Since we were moving around so much, it was easier for me to just say, “I’ll step up and handle the gaps these two weeks” rather than put myself first and say, “You know what, I need some time for myself.”

I’ve been telling people that the ideal amount of parenting is not 100%, and the ideal amount of work is not 0%. The hard thing is figuring out what the right balance is between those two points for you and noticing when those needs shift. For the first two years, I could handle a lot of parenting and also work deeply on my writing at the same time. Sometime after my daughter turned two, I didn’t have much left to do the creative work, but I failed to admit this to myself. Being a parent has been incredibly humbling. Every month has brought a new little person with updated needs, preferences, interests, skills, and demands. And as she grew, I did too, convinced I could just keep handling more and more.

My curiosity drives a lot of this: What happens if I put family before work? I keep asking that question, and going in one direction always wins out over the other. I am happy about the results too: I’ve become much more resilient, caring, connected, and silly, and the dad that I always wanted to be. I am so much more ready for my second than I ever was with my first, and that feels really good.

But stepping back, I know that I need to put myself first a bit more in the coming years, too. To put my oxygen mask on first so I can go do my good work and come back recharged, rested, and inspired. I think any parent can relate to this challenge.

People always ask me to write a book about parenting, and I always tell them I have no idea what I’m doing.

The most confident parents seem to be the ones without kids, followed by those with 1-year-olds, and so on. The beauty of being a parent is that if you let it, it will break you open over and over again. I’m in the throes of letting that happen to me, and the best part is feeling all the joy that flows when you truly release yourself. I am definitely not going to write a book about parenting unless someone pays me a million dollars, but I can leave you with this: Parenting is a humbling, heartbreaking, and joyous journey, a potentially more direct spiritual path than psychedelics or meditation. It’s a journey that pushes you toward the edge of what you can handle over and over again, and if you let it happen to you, allows you to become more of who you are. I’m still in the throes of it all, and I’m not quite sure what will unfold next. But I am open and ready.

Two weeks in a row, nice. Am I back? Maybe? I think so? Let’s see.

I’ve been doing some form of public writing since 2015. I’ve somehow figured out how to hack a living doing things like writing books and launching premium art editions of my book. If you like what you read here, you’ll probably enjoy my books The Pathless Path and Good Work:

If you’d like to join a virtual community of others on “pathless paths” from around the world, and get access to courses, tools, and other resources I’ve created over the years, you can join The Pathless Path Community. Our recent WhatsApp community is very active if you like hanging out on messaging apps instead of Circle.

Some things I endorse:

• Readwise is offering 2 months free (I use it for book notes and reviewing highlights). Or two months free on

• Readwise Reader, which I use for RSS reading and epub reading

• Crowdhealth, an alternative to US health insurance that I’m still using while abroad

• Postbridge: A social scheduling app created by a reader without crazy upcharges for more accounts

• Kindred, a home-sharing app

• Collective for handling your S-Corp accounting needs, and Nat Eliason’s Build Your Own AI Apps course

If you received this and find yourself in a state of outrage, thinking, “What is this?” I strongly encourage you to unsubscribe below. It is your God-given right, and there is plenty of other good stuff online.

A reminder: I don’t check unsubscribe alerts and never look at my subscriber list. So if you feel like unsubscribing, you can do so below.

This is the longest stretch I’ve had without consistently writing the newsletter since 2018. A few reasons:

1. Mini sabbatical: In January, I decided to take a mini-sabbatical. This was partly because of participating in Traveling Village, a four-month trip with 20 families across three countries, something I wanted to sink myself into fully, At the beginning of the year, I was feeling a bit stuck and lost with my writing and work generally. When I’m feeling stuck, my instinct is to do less. I think that was the right instinct, and I’m happy to report I’m finding my way out of the long shadow of a 2025 slump.

2. Agentic Coding: Getting unstuck was almost directly linked with the dabbling I did with agentic coding tools. After a call with in January (the day before I started my sabbatical) I started dabbling with agentic coding tools and ended up getting nerdsniped by the possibilities and reality that I could now refactor my entire digital stack (more below) for how I’m working. In the months since, I’ve rebuilt my StrategyU business, moved six sites off WordPress, built a custom bookstore, and automated Amazon ads for my books.

3. Shift: The experience of shipping so many projects and taking action on so many things that were previously too daunting or too hard was thrilling and disorienting. I had my “holy shit, AI is going to change everything we know about work” moment several times in the past couple of months.

   1. While many people who have had a similar awakening are quick to pronounce that you “only have six months” or that “you need to make money so you don’t become part of the permanent underclass,” my position is closer to wonderment and lots and lots of unanswered questions. I sense many people are reasoning from exuberance rather than allowing the uncertainty to wash over them.

Today’s post is a reflection on how I’m thinking about all of this, especially AI, work and the indie path in the context of my new AI-enhanced superpowers.

Embracing Full-Stack Weirdness

The best phrase I’ve ever found to describe my ideal path is "feral free agent." It’s perfect for someone who doesn’t like to be pinned down. I enjoy shifting between projects and identities. Some days I write. Some days I code. Some days I goof off. Other days I take a nap. I may try to make money, but it’s not my only aim.

Another more legible frame on this same idea is Tiago Forte’s “full-stack freelancer” from 2017:

When I first stumbled upon Tiago’s framing of this in early 2018, I found it incredibly appealing. I had just finished six months where I was in freelance mode, trying to prove to myself that I could make it on my own. But I didn’t want to be just a freelancer. As Tiago put it in the original article:

Full-Stack Freelancers respond to technology as an opportunity, not a threat. They leverage software-as-a-service and online platforms to vertically integrate a “full stack” of capabilities, instead of focusing on one narrow function. This allows them to capture a much greater percentage of the value they create, instead of giving it away to gatekeepers and distribution bottlenecks.

As an overeager early adopter of technology, this definition appealed to me. I wanted to embrace the latest tools not only because I liked tinkering with them but through using them, I would see and feel new possibilities for working. I remember the first time using Zoom thinking wow, remote work is now legit. Same thing with Stripe. Payments were hard and annoying and then they were solved.

While much of Tiago’s formulation was right, there were hidden constraints if you wanted to scale. Each platform meant new possibilities but also unique constraints. Each one forced you to repackage your work and sell it in specific ways. The mental overhead of fitting your work into the strong opinions of different platforms meant economies of scale were hard to find as a solopreneur. And these platforms only became more distinct and less interoperable in my time on this path. It’s no surprise that Tiago and many others who started in the solo indie mode eventually built teams.

While the indie mode has enabled me to hack a living and make a decent income for the last nine years, the constraints across various algorithms, systems, and platforms have become increasingly taxing. Each social media platform now nudges you to create natively and no longer reliably shares your work with followers unless it is rated as engaging by the algorithm

Platforms and tools like Circle, Substack, Thrivecart, Podia, Gumroad, Stripe, and Teachable were/are amazing and enabled me to make money in ways that were impossible ten years ago, but each of these platforms has a business model that wants me to package my work and make money in certain ways. I’ve used Circle for my community platform, but struggled for more than a year trying to sync it with Substack’s payment infrastructure, wasting endless time updating member access lists, before eventually abandoning Substack subscriptions and moving my community to a one-time fee to eliminate the admin work. Last year, I gave up logging into the platform and engaging with people and moved the community chat to WhatsApp because my revealed preference was that Circle was energy draining for me. The vibe and energy of the community completely changed overnight. I'm somewhat better aligned, but I’m still at the mercy of WhatsApp’s roadmap and product choices. The list goes on. On Teachable, I’ve had a lot of success with my Think Like A Strategy Consultant course, but I have felt unmotivated to make changes or upgrades because the platform had become clunky and slow.

Each platform, product, and brand I created became its own world. Not only would I need to think about each product in different ways, I’d also need to embrace a different persona within each of those ecosystems.

I was a full-stack freelancer in theory but in practice was spending lots of time on admin and the mental overhead of trying to manage all my distinct products and related personas. I was frustrated by this but also by the reality that the way to “win” in this game is to flatten yourself into what the platforms and algorithms want. You could only be truly feral if you wanted to be broke. Most of the creators and online writers that successfully played this game either outsourced the work to other people or were naturals at hacking the increasingly default path energy of the self-employment world.

At the beginning of the year, I was sort of burned out, thinking that I really needed to do something drastic.

For me, drastic meant doing less.

So I declared a mini sabbatical to pause several projects, look around, and see what might pull my interests.

Somehow, within a week, I had my first interaction with Claude code.

Holy shit I have superpowers.

Rewilding the stack

Something I haven’t seen talked about much is how agentic coding enables unique tooling built around one’s unique preferences for working.

With SaaS apps, we are constantly pressured into upgrading for the next tier of features that promise to eliminate the annoyances of the current tier. Except this never stops. You upgrade and then you find a new roadblock. Then you start adding up the costs and realize that the company doesn’t really want a weird indie creator like me on the platform. They want me to scale. They want me to do more monetization. You know, like a real business. You send a text to your group chat and say, “I’m thinking of switching off this platform, who has recommendations.” Everyone responds back with the thing they hate about their platform and you realize, this is not worth it. I must just accept my current platform.

Now, building from scratch, I can build exactly what I want designed around some of the weird tradeoffs I like to make, and when things shift, I can make subtle tweaks at the underlying development layer.

The result of this has been a major shift and vibe shift internally.

I’ve felt a lightness and an excitement about the possibilities of what I can create that I haven’t felt in a while. Part of this is that an endless list of things that I previously wanted to exist moved from too much work/too hard/too costly bucket to now a quick prompt to develop an MVP before deciding if I want to go further. As a former consultant who loves being in the flow of endless iterative work, this is great. I love it. Another part which makes this so fun is that I’m reaping a dividend from optimizing around laziness and not grinding over the past few years. I literally kept saying to myself, something interesting will emerge, I’ll eventually find the way forward.

In December, the bar of coding skills needed to build my own custom stack suddenly dropped and I was upgraded to software engineer. What was impossible or too much work a year ago is now not only possible but fun. I spent ten days completely rebuilding my StrategyU course, moving off Teachable, saving thousands of dollars a year, while also reviving my interest in running the business. Last year I was thinking about finding someone to run it, selling the business or winding it down. Now I’ve rebuilt the course again, I’m adding lectures, and am feeling more energized than ever. My chief of staff, Claude, is an excellent coworker.

The new platform is built around the behaviors and actions I specifically want to be taking. With everything I ship that delights me, I am not only improving the platform, I am increasing the odds of wanting to continue to maintain and improve things in the future. This is the limit of the former SaaS/Platform world: any tension with defaults leads to compounding disinterest and/or the requirement to outsource to a better aligned human. If I don’t like how my current platform is operating, I don’t need to find a workaround or a hack (mentally taxing), I can permanently improve the situation.

Working with tools like Stripe, Mux, Vercel, Cloudflare, GitHub, and leveraging APIs and open source libraries, I can start with my ideal way of working and then ask the coding agents if it’s possible, and if not, give me further ideas. While rebuilding Teachable, I learned more about coding and software development than I have in the last ten years. This “reverse sensemaking” (ship and then figure out what you did) is an underrated aspect of these new tools.

The more I’ve shipped, the more I’ve figured out, and I am seeing things in a different way. Seeing like an agent if you will. But it’s not the tools that excite me themselves, it’s the possibilities for how I run my business, and the degrees of freedom it allows me for how I show up in the world.

A 1:1 bookshop

A quick example is the custom bookstore I launched at books.pmillerd.com. For the past few years, I’ve been frustrated with the inability to really create a direct channel to my readers. I’ve always wanted to offer a place where people could buy products directly from me and be able to deliver them in ways that I’d want to receive them as a reader. I’ve dabbled with Shopify and that works quite well for managing the logistics of my hardcover but it never felt right for setting up direct distribution of the digital versions of my work.

Here is the Shopify setup. Its fine, it works, but as you can see on the right, its just an uninspiring downloadable list of files.

I’ve spent the last couple of weeks tinkering and now have a platform that does many absurd things:

• Easy access to my digital books in all formats

• My own web reader that has text-to-speech that sounds pretty great (via Amazon Polly)

• Has a workflow that allows people to embed custom dedication pages into my EPUBs and PDFs when they gift them (coming to paperback soon)

• Automatic syncing with Lulu’s API for ordering paperback books shipped around the world with live syncing of shipping rates

• The backend tooling to easily release limited edition drops of my printed editions or any other physical product (if I wanted to ship a custom foreword, or anniversary edition, etc.))

• Automatic discounting if you gift multiple copies of my book to others

• Highlights and notes with simple export (adding readwise connection soon)

• A gifting page where I can give away free digital editions and that also adds 5 copies every time someone leaves a tip or gifts a book to a friend

Here are a couple of the screenshots

This is all absurd and unnecessary and most of this may not make me any money. But it absolutely makes me laugh and smile and I find it incredibly fun. If it makes someone else laugh too then my job is done.

This was a lot harder than the one-shot AI bros make it out to be and sometimes it takes many attempts to get something to work, but with each session I’m able to stay in the loop, experiment with tools like AWS, Cloudflare Workers, Resend and MXRoute, while also having a clearer sense of what I want to be doing. It’s like continuously peeking around new corners.

I’ve been thinking a lot about Venkatesh Rao’s framing of the “Clutch Class,” the workers who are neither part of labor nor capital, as many aspiring feral free agents would. In his book Art of Gig (which is still very underrated for today’s times), he frames the mode of working and exploring in which I find myself now:

A fun tongue in cheek rallying call at the end pumps me up but right now it doesn’t feel like the future will belong to me at all.

I sometimes wonder if I’m insane, tinkering away on my own stuff, passing up the continued wealth grab that many of my friends and former classmates are gladly participating in.

It seems like the capital class is going to take it all and anyone willing to conform themselves into a capital shaped worker. That’s certainly terrifying and I’m not going to dwell on the implications of that here, almost every media institution is pounding us with what is bad about AI.

All I’ll say is that if you dig deeper with these tools, there is a promising alternative path that you can take. A chance to really lean into weirdness, feralness, and aliveness.

Which is the best way to find the gaps in the emerging and evolving economic frontier.

Time to go full pathless.

Who’s in?

#2 A small side newsletter

I started “Modern Publishing” to share my deeper dives into the publishing industry. This is an experiment, and we’ll see if I want to keep it running. I may just merge it back into this newsletter, we will see. But the first post is a deep dive into my foreign rights deals and how much I make from each book (hint: not much!)

Modern Publishing with Paul Millerd

I make 20 cents per book in India (I share everything about foreign rights for The Pathless Path)

Hey there…

Read more

a month ago · 4 likes · Paul Millerd

Modern Publishing with Paul Millerd

A front-row seat as I try to make sense of this ages-old industry as technology demands new possibilities for authors

Hey there

I’ve been doing some form of public writing since 2015. I’ve somehow figured out how to hack a living doing things like writing books and launching premium art editions of my book. If you like what you read here, you’ll probably enjoy my books The Pathless Path and Good Work:

If you’d like to join a virtual community of others on “pathless paths” from around the world, and get access to courses, tools, and other resources I’ve created over the years, you can join The Pathless Path Community. Our recent WhatsApp community is very active if you like hanging out on messaging apps instead of Circle.

Some things I endorse:

• Readwise is offering 2 months free (I use it for book notes and reviewing highlights). Or two months free on

• Readwise Reader, which I use for RSS reading and epub reading

• Crowdhealth, an alternative to US health insurance that I’m still using while abroad

• Postbridge: A social scheduling app created by a reader without crazy upcharges for more accounts

• Kindred, a home-sharing app

• Collective for handling your S-Corp accounting needs, and Nat Eliason’s Build Your Own AI Apps course

If you received this and find yourself in a state of outrage, thinking, “What is this?” I strongly encourage you to unsubscribe below. It is your God-given right, and there is plenty of other good stuff online.

A reminder: I don’t check unsubscribe alerts and never look at my subscriber list. So if you feel like unsubscribing, you can do so below.

He’s got a new book coming out, titled Dirtbag Rich, in which I play a very minor role, based on a convo we had on his podcast last year.

He pitched me on writing an essay for the newsletter and said, send me what ya got. I liked it. Especially this frame:

Where are the people who have found ample time, money, and purpose in their 20s, 30s, and 40s? What about those with children? What about those who don’t particularly love dirt? What about those with difficult upbringings, or constant anxiety, or, or, or… The stories are all there.

I also just love the title Dirtbag Rich pairing. It might be better than Pathless Path. The combo of “dirtbag,” a term often embraced by climbers who build their lives around bare minimum living, with rich, is nice.

Without further ado…

Time, money, and purpose

If you’re a Paul Millerd fan, I suspect you already think differently about time, money, and purpose.

Time: You try hard to remain in control of the hours of your day, week, and year. Perhaps you work regularly but part-time, intensely but seasonally, or possess an otherwise normal job that allows significant breaks. The time of your life does not belong to your employer, your clients, or anyone else—it is yours alone.

Money: You attempt to earn a substantial amount relative to your efforts, perhaps via a high hourly wage, big payouts after big gigs, or some version of (so-called) passive income. Paired with low expenses, you can subsist happily on a lower income—sometimes even “poverty wages”—and enjoy the spacious freedom necessary to do what you love.

Purpose: You really, truly attempt to “do what you love,” right here, right now, in your one life on Earth. Instead of making purpose wait for the weekend, you actively seek it, compensated or not, day in and day out. Because why else would you so carefully manage your time and money? What would be the point?

While the status quo tells you to earn money at the expense of time and purpose—two resources you’re supposedly meant to reclaim in retirement (a.k.a. the pre-death siesta)—you have resolved to take a different approach.

Some call this the pathless path, a label I quite enjoy.

For me, another term fits even better: dirtbag rich.

What’s a dirtbag?

The first dirtbags were hardcore rock climbers in Yosemite Valley who camped illegally, showered infrequently, and scavenged for meals. When they needed money, they’d leave the Valley to paint houses, wait tables, teach skiing, or even take a desk job: anything to refill their coffers and get back to the big walls. They lived like bums in pursuit of the good life.

Today dirtbags come in many flavors, not just “climber” and “white male.” Some are trail runners, mountain bikers, long-distance hikers, backcountry skiers, cross-country cyclists, or endless-summer surfers. Others are dancers, slackliners, or perpetual travelers. All are passionate. All are extreme. None are what the mainstream would describe as “balanced.”

Some dirtbags live in vans, trucks, or tents. Others couchsurf, hitchhike, or stay with friends. Some do pay rent: just not very much, and not for very long. For dirtbags, full-time, full-price rental contracts lie somewhere between a luxury and an obscenity.

Many dirtbags come from middle-class security. Some come from upper-class privilege. Others come from next to nothing.

All dirtbags revere nature, movement, and thrift. All struggle to fit into conventional society. All want to be left alone to do what they love, while they also yearn for membership in a tight-knit community of the similarly obsessed.

Many who lead such lives aren’t aware of the label “dirtbag.” Of those who are aware, many don’t welcome its associations. I understand their aversion, but I like the term.

To me, being a dirtbag simply means that you’re too busy following your bliss to worry about a little dirt under your nails. It means you’re doing something right.

Freedom = moving your body swiftly through nature

As I recount in my new book, Dirtbag Rich: High Freedom, Low Income, Deep Purpose, I never made a very good dirtbag.

My attempt to hike the Pacific Crest Trail at age 22 ended two weeks after it started, catapulting me into a multi-year crisis of commitment. I failed to live happily outdoors like a “real” dirtbag, yet I was also incapable of holding a “real” job like a normal member of society.

Three months of soul-seeking in South America revealed the first glimpses of an answer: I needed to take the middle path. I needed to craft a new way of living in the liminal space between hardcore dirtbagging and conventional wealth-seeking.

Because the truth was: I loved sleeping in the dirt, in a bag. I loved it when I was 22, and today at 43, I still do. Living like a hobo in the mountains is one of my “peak experiences,” and that’s not going to change.

Anytime I move my body swiftly through nature, in fact—whether backpacking, day hiking, trail running, bicycle touring, or swimming in alpine lakes—everything tastes, smells, sounds, and feels more intense. The same goes for international travel. Whenever I’m in motion, I remember more details, and everything feels more “real.” Daily life in cities, in contrast, is too easily forgettable and “unreal” (with the exception of social partner dancing: the one thing that keeps me circling back to big cities).

If you’re anything like me, then you, too, face a series of dilemmas:

• You derive profound purpose from moving your body through nature, yet you’re not ready to live like a total dirtbag.

• You won’t be a mere weekend warrior, nor will you drop out of polite society.

• You crave wilderness immersion, long-term travel, retreats with friends, and other transformative experiences, while also desiring to put something away for the future.

You are an irrational, implacable, exuberant creature who wants it all—time, money, and purpose—with very few compromises. Heaven help you.

Impossible contradictions are fun

As I navigated these tensions throughout my twenties and early thirties, many questions remained. How could I earn enough while only working part-time? How would I manage without a home base? What if I wanted a family? And beneath them all: What if I was making a giant, life-shattering mistake by not swallowing my discomfort, burying these impossible desires, and getting on with a normal existence?

I knew that every path has trade-offs. If I lived for adventure, I might not have kids. If I had kids, I’d certainly take fewer adventures. Travel would change me, just as rootedness would change me. Working for myself might be the best thing I ever do, and turning my passion into a business might suffocate it.

No one can have it all. But maybe, just maybe, I could have more than the world promised.

And—spoiler alert!—I have.

I ended up creating a little travel company for unschooled teenagers: one that let me share my love of travel and nature with delightful young people while also earning decently in a brief period. I dedicated my newfound free time to nature, dance, travel, adventure, and writing books about self-directed learning. I did not start a family, but I did develop deep friendships across the world and find profound meaning in playing a unique role in the lives of other people’s children.

Attempting to live dirtbag rich means navigating a series of seemingly impossible contradictions. Some of these contradictions are very real—like balancing freedom and romantic attachment—while others are but smoke and mirrors. As with any serious attempt to live differently, fear of the unknown stops most from ever trying. Nor is it a mere privilege issue, as wealthy people are often the most chained to convention; the ideal setup may be moderate privilege + high idealism.

Yes, it’s possible. Yes, it’s hard. On any pathless path, it’s a question of what kind of glory you crave and what kind of difficulties you can face down.

How (and where) to begin

Ask yourself that age-old question: “If I suddenly had [ridiculous sum of money] in the bank, how would I live differently?”

If the answer is “not much differently”—if you’d reduce your working hours a bit, for example, but not change your work—then you’ve already struck a magical balance of time, money, and purpose. Keep it up!

If the answer is “VERY, VERY DIFFERENTLY”—if you’d pursue a whole new vocation or wander in the woods indefinitely—this indicates a need for change, and a possible new direction for your life.

There’s no silver bullet for this kind of stuff; distrust anyone who insists otherwise. Rather, you need a wealth of examples.

This is what Paul has achieved with his books and the Pathless Path Community, and it’s what I’m attempting with my dirtbag rich interview series (which includes Paul). Where are the people who have found ample time, money, and purpose in their 20s, 30s, and 40s? What about those with children? What about those who don’t particularly love dirt? What about those with difficult upbringings, or constant anxiety, or, or, or… The stories are all there.

To begin living differently, you need a bunch of role models. None will exactly match your background, values, risk tolerance, or other constraints. Each will have something to teach you. Listen to their stories: the long version, not the soundbyte. When one resonates, reach out and ask a few follow-up questions, as a 22-year-old adventurer from Chicago did with me yesterday. (Remember the promise of the early internet: You can just find interesting people and connect directly with them!)

This is how any pathless path—or dirtbag rich life—begins and evolves. Watching, thinking, feeling, researching. Getting honest, getting vulnerable, getting in touch. And at some point: making a big move. What that specific move is, I cannot say. All I know for sure is that at some point, you must stop gathering data—and act.

As for me, I’m going to keep dancing, cycle touring, working with unschooled teenagers, and losing myself in the wild places of the world. I’ll keep visiting friends and family, showing up for other people’s kids, writing for a small but engaged audience, and remaining open to the possibility of another big pivot.

This is a life I wouldn’t dream of trading away for a pile of money, the myth of retirement, or some other distraction. It’s far from perfect, it’s still fraught with uncertainty, and it could all end tomorrow. But we’re not here to win the game of life—we’re here to play progressively more interesting levels. Onwards.𖤓

It’s Paul Again. If you want to check out his book, it’s $4.99 on Kindle or on his website. I already grabbed one.

This is the longest break I’ve taken from writing this newsletter since the birth of my daughter three years ago. It wasn’t the contemplative kind of break I would often take early in my journey, but it was still refreshing. It was a useful practice to take a step back and assess all the various projects I’m involved in and figure out where I should be spending my time in the future.

This mini-sabbatical also coincided with a few other big life events.

First, I’m participating in a five-month experimental travel group called the traveling village.

We are in the second location, in Taiwan, and have really enjoyed the experience so far. We spent the first five weeks in Vietnam and it’s been a possibility-expanding trip. The payoff to having other families who are location-independent around is pretty amazing, it’s something we’ve been missing for a couple of years. Right now, we’re living with another family in the same house with a four- and six-year-old overlooking the ocean, with nine other families within a three minute walk. It’s convinced me that hyper co-location is a cheat code for taking the stress away from having young kids. It turns out the “village” idea basically works, it just takes quite a bit to get others onboard.

More thoughts on this soon but please send me questions.

Second, book, Made in Taiwan, was released in traditional Chinese in Taiwan last week.

This has been a huge project for her, and I can say with complete confidence that I think she nailed it. With the help of AI translation tools, I was lucky to be able to collaborate with her on the developmental editing. This was certainly a challenge as I probably pushed her a bit too hard at points, but every time I did, she would come back with a rewrite that blew me away. I am lucky to be married to Angie and am always amazed at how she continues to grow and never gives up despite the challenges she faces. We are currently working together on an English translation too, which will come out later this year.

In the meantime, you can grab a copy to gift to the person in your life that reads traditional Chinese. Or, you know, you can buy it too, because there are no laws against you buying a book you can’t read:

Grab The Chinese Version

Finally, we have to talk about Claude Code.

Right before I took this little break, I had a call with , a fellow tinkerer and writer I’ve known since the dog days of the pandemic. The call we had was mind-blowing and I especially appreciated how Alex is approaching using the tool as a creator-first, not as a hustle bro telling everyone “you’re already late.”

This is an unsolicited ad for Alex’s resources on codeforcreatives.com - Alex is a genuinely nice and generous person and creative force and excellent writer. It’s been cool to see him find his thing and be so excited about this, so go there and support him or set up a call if you want to be Claude Code pilled.

I had dabbled with Cursor and Claude Code a bit last year but they never worked and I’d always face too many roadblocks to executing any of the projects I’ve wanted to work on.

But this time really is different. With the new models and UX upgrades, Claude Code, whether in the app or command line, is one of the most powerful tools I’ve ever used. In increasing leaps of boldness, I’ve passively executed on a number of projects in some of the free time I had due to the the efficiencies of scale of traveling with many other families whose kids want to play with my daughter:

#1 A health dashboard: I have a folder of my lifetime health records, and for the first time, Claude was able to easily build me a custom dashboard where I can notice issues, and also brainstorm any problems I’m having based on all this information as context. I suspect everyone will have something like this within a year or two.

#2 Blog Rebuilds: Completely transferred three of my sites, pmillerd.com, angiecreates.io, and strategyu.co, to a static site, each in about 4-5 hours of work: I published a skill on my process here.

#3 Teachable Clone: After doing StrategyU blog rebuild, I started thinking: could I replace Teachable, which was hosting my online course? Part of the reason I wanted to attempt this was that the platform literally hadn’t made any meaningful upgrades in years, and the tracking I was doing for ads didn’t work at all anymore. In less than ten days, I went from tweet to launch.

The final stack was mostly free dev tools: Next, React, Typescript, Convex, Mux, Posthog, Resend + Stripe. It sounds complex but for someone who’s been dancing around these tools for years but could never quite do anything meaningful, it all sort of clicked and fell into place. I just migrated all users and downgraded my Teachable subscription yesterday.

#4 Publishing Chinese EPUBs and Print Books: Angie is self-publishing her book in Taiwan. We have a partner helping with print distribution in Taiwan but had to setup the EPUB and print-on-demand versions everywhere else. This was much more challenging than I expected because Traditional Chinese is typically read right to left, top to bottom. A typical page looks like this:

It turns out that the support for this style EPUB is not very widespread and many books in Taiwan don’t even do it because of technical limitations!

Claude Code to the rescue. Over a couple of weeks I was able to:

• Reformat a beautiful EPUB as seen above, 100% via code, keeping the original text intact as well, including custom versions for Apple, Kobo, and Readmoo.

• Produce a .docx version for Amazon Kindle, as they don’t support vertical Chinese yet, and

• I was able to solve 3-4 gnarly PDF issues on documents we needed to submit for print-on-demand to IngramSpark and Lulu

The crazy thing about these things is that in the past they would all require specialized paid contractors to execute. I estimate we likely saved $1000-$2000 by doing all these things on our own (not to mention made a better product).

#5 Then, I shipped a website in Chinese without fully knowing the language, all via Claude Code, building out a bunch of cool features, like automated testimonials and a smooth process for digital book gifting based on a code.

#6 Finally, a fun experiment, an agentic Store for My Books: Half-joking, half-serious, I decided to launch a store for agents to buy my book:

Anthropic is supposedly going to pay out $3,000 per book that they pirated, so I want to make sure these big labs have the chance to grab my book for a little cheaper:

It’s clearly the way the web is going, designing interfaces, APIs and processes that enable agents to interact with your products and work. Shopify has recently just made agentic shopping a live feature in the last week. So all you need to do is tell your agent to come to my site and follow the simple instructions:

Browse the catalog at https://agent.pathlesspublishing.com/api/catalog

To purchase, POST to https://agent.pathlesspublishing.com/api/purchase with:
{
  “slug”: “the-pathless-path”,
  “email”: “YOUR_EMAIL”,
  “buyerType”: “personal”
}

This returns a Stripe checkout URL. Open it to complete payment.

When the purchase is made, it automatically injects a license and hash in the EPUB, MD, and JSON files with terms and specific instructions on how to use the book and how to source it (encouraged).

While this was a fun little experiment (it took 3 hours to code up) it made me realize that there is probably a lot more potential in publishing to build a new stack for selling books, especially for indies like me who won’t be slowed down by traditional publishers. This also makes me incredibly bullish on digital formats of books, mostly because they will be easier to acquire and self-DRM tools will be easier than ever to use. Likely more on this throughout the year

I’m feeling very energized

While it looks like I was working a lot, it really didn’t feel like that. Most of the above projects with Claude Code did NOT take much focused energy. I dabbled on them here and there, during naps, at night, and in 2 or 3 focused work sessions. It certainly required strong basic foundational knowledge of the various tools I was using, but that is something I had in spades after years of tinkering and having fun online.

For someone like me, who doesn’t want to grind my way to success, these tools are incredibly powerful. They remove so much friction and annoyance from launching digital experiments, sites, and products, that I’m rethinking many of the things I thought I’d never do. On top of that, I’m really thinking deeply about what work means in this new reality. This way of working is definitely going to change knowledge work, but I need to think a bit more about it.

Personally, my mind is overflowing with ideas and feeling more open and excited than I have been in a while.

Do sabbaticals always work this way? Aligning with what the universe is ready to tell you? It certainly seems like that sometimes and based on what many of you have shared, it does..

With the publication of Angie’s book it also feels like a new chapter is finally starting.

The past two years have been incredibly hard for me. I’ve been doing a lot of childcare, by choice, and really been enjoying it. But man oh man, has it been a growth experience. I’ve had to grow emotionally, learn how to ask for what I need in my relationship, and also learn to feel the feelings that are easy to suppress when you are trying to hold it together for everyone else.

Angie’s book was something I really believed in and felt was an important core project for our family, despite it being something that may not bring financial rewards. I am glad we oriented our family and life around it. Taking a step back from my work since Good Work was published in October 2024 has been an interesting experience. I’ve definitely found the limit of not enough work and it’s cemented my belief that the right amount of childcare for a parent is not 100% and the right amount of work is not 0% either. The balance is somewhere in the middle.

Through the traveling village, a year of nomadic living, working closely with Angie on a creative project, stepping up as a dad, and growing as a family, I am starting to feel more confident about how the next chapter of our life may unfold.

But as always, it is exactly that, an unfolding.

But after this break, I actually feel like I'm letting things unfold again rather than trying to take off the wrapper by force.

That’s it for today and I’m incredibly grateful for you all.

Keep dreaming big, taking chances, and moving toward the life that matters to you.

See you soon.

-Paul

P.S. I have been having a lot of issues with Substack delivery over the last six months, and I’ve been having large unexpected unsubscribes after sending each issue. It’s been weird, though I may have found the source of the issue. I had my subdomain for substack “proxied” on my DNS which Claude tells me might have flagged my domain for months. If you have had any issues receiving my email or are seeing this one for the first time in a while, let me know. Hopefully everything is fixed now.

Yo.

I’ve been doing some form of public writing since 2015. I’ve somehow figured out how to hack a living doing things like writing books and launching premium art editions of my book. If you like what you read here, you’ll probably enjoy my books The Pathless Path and Good Work:

If you’d like to join a virtual community of others on “pathless paths” from around the world, and get access to courses, tools, and other resources I’ve created over the years, you can join The Pathless Path Community. Our recent WhatsApp community is very active if you like hanging out on messaging apps instead of Circle.

Some things I endorse:

• Readwise is offering 2 months free (I use it for book notes and reviewing highlights). Or two months free on

• Readwise Reader, which I use for RSS reading and epub reading

• Crowdhealth, an alternative to US health insurance that I’m still using while abroad

• Postbridge: A social scheduling app created by a reader without crazy upcharges for more accounts

• Kindred, a home-sharing app

• Collective for handling your S-Corp accounting needs, and Nat Eliason’s Build Your Own AI Apps course

If you received this and find yourself in a state of outrage, thinking, “What is this?” I strongly encourage you to unsubscribe below. It is your God-given right, and there is plenty of other good stuff online.

A reminder: I don’t check unsubscribe alerts and never look at my subscriber list. So if you feel like unsubscribing, you can do so below.

A couple quick shouts:

• is publishing her book Made in Taiwan in Traditional Chinese next week! The final product is incredible; it’s one of the best memoirs I’ve read (I am biased, but I think I will be quickly validated by readers!). We’re excited to share it in English after we co-translate it later this year, so stay tuned. If you read Chinese or would like to grab a copy to support her, all the links are here: Made in Taiwan.

• You can now purchase notebooks, shirts, my paperbacks, and Angie’s books all directly from my Shopify store.

Below is a guest post/Q&A from Holly Gabrielle, who recently left the creator world to go all in on trying to become a top Hyrox athlete. I love highlighting new paths that exist in the world, and this one definitely qualifies.

Ok, you just quit your job, which was working on Ali Abdaal’s team, after reading Good Work. What is going on over there? Is Ali getting ready to ban my books?

Haha, to be fair, Ali might think twice about giving out free copies of Good Work to members of his team in future. But my departure was the least dramatic thing ever - I simply sent a Slack message to Angus (Ali’s general manager) basically explaining that I wanted to go off and do my own thing … or in other words, quit a perfectly stable copywriting job to chase a dream of becoming one of the top 15 women in the world at a sport I’d never actually competed in yet 😅

Absurdity aside, being part of the Ali Abdaal team is honestly so dangerous because you start believing you can do things, and I wasn’t even a full-time team member - I was freelance, working 3 days a week - yet I still caught on.

Like many of us, I was guilty of procrastinating on ideas, shutting them down, telling myself I wasn’t good enough, or just learning more and more information, convinced that I just wasn’t ready yet. But Ali talks so much about taking action and not letting your emotions or fears hold you back - whether it’s starting a YouTube channel or a lifestyle business or even something as small and personal as going on your first date - and when you work for him, it’s pretty hard not to eventually listen.

So, like many other team members, after 2 years working with Ali, I’d heard enough. I took his advice a bit too literally and decided to go all-in on trying to become an elite Hyrox athlete (and simultaneously return to my content creator origins).

You’re going to pursue being an “elite athlete”? That sounds awesome. I suspect needing more time for training, rest, and recovery is part of it, and a job doesn’t help with focusing on that. Any other reasons?

Yep, you’re pretty much spot on. Time for training and recovery was a huge factor, and I’m hoping this allows me to make much faster progress. But it wasn’t just about the physical time - it was a mental energy thing too.

Realistically, I could’ve kept my writing job with Ali and also gone all-in on this lofty (and pretty scary!!) goal of becoming an elite athlete. Besides, working with the team was such a great experience - the flexibility was incredible, I was always learning new nuggets of information, and the people were amazing.

But I know myself well enough to know that my brain doesn’t really switch off - and that comes at a cost.

Even though the team never gave me any super strict deadlines, I’d always push myself to write one more email before 5pm, shorten my breaks to cram in a bit more work, or find a way to level-up in my role. It was exhausting.

And it wasn’t until I came across ideas like essentialism and the “Hell Yeah or No” framework by Derek Siver (again, all through Ali) that I started to question how much of a toll it was taking on me. I also realised that it was stealing a lot of mental energy away from my runs and workouts. I’d often blindly go into a session and wonder why it felt hard. I left no time to reflect on my sessions, properly plan my workouts, or even just celebrate my small wins.

So long story short: I finally decided to step back. Yes, it’s probably been one of the hardest things I’ve ever done because saying no or quitting doesn’t come naturally to me, but I’m excited by the challenge of finally doing less to hopefully get more out of the things that mean the most to me and have the potential to completely change my life.

Are you already making money from your athletic pursuits (career, path, passion, what else do you call this?!), and how did this impact your decision?

I’d love to say yes, but the answer is no, sadly 🙈 Right now, I’m not making any money from this.

Just for some context: I’ve been “influencing” for about 10 years now. I started my first YouTube channel when I was at uni, and ever since graduating, I’ve pretty much been documenting my entire life on the internet. As a result, I have a couple of affiliate links that are earning me a bit of money right now, as well as some passive income from my old YouTube videos … but we’re talking a few hundred pounds a month.

Plus, they’re not exactly aligned with my version of good work going forwards.

Ideally, I’d love to be a full-time sponsored athlete one day - that would be absolutely unreal. And alongside that, I’m rebuilding my personal brand from the ground up.

I’ve recently started a joint YouTube channel with my partner, Angelo, where we’re documenting our journey to the Elite 15 in Hyrox, and I’m rebranding my Instagram content to be specifically within this niche. The goal is to make this financially sustainable long-term, but right now, the income from all of that is pretty much zero.

Don’t get me wrong, it’s scary not having a monthly income right now - like really scary. It was also a pretty big concern of my parents when I left my job, but I’m proud of myself for not letting financial worries stop me from going after some big goals that genuinely excite me.

What is the link between training, sharing your journey online, and how those have evolved together over time?

Love this question… although the answer isn’t super straightforward.

If we go way back, I grew up dancing competitively and have always been super interested in my own health and fitness. In all honesty, I always thought I’d live my life as a professional dancer, just like my mum, but I guess things didn’t work out that way oops - ended up going down a completely different path and studying biology at Cambridge instead.

This is when I started my first YouTube channel (2016), and even though my vlogs were heavily centred around my chaotic student life and studies at Cambridge, food and fitness were always underlying themes.

Sadly though, I experienced some pretty deep and chronic mental health issues that lasted pretty much the entirety of my teenage years and early twenties, which turned my love for fitness into something pretty toxic. I was in denial for years, and this made it really hard to be vocal about health and fitness online, because deep down I had my own things to fix first.

At the start of 2025, I stepped back from YouTube and social media a bit and decided to work on myself - focus on my writing job with Ali, spend more time with the people that matter most to me, and finally fix my relationship with food and exercise. When I could finally see how damaging this dynamic was, I thought it was best to never mention it online ever again. But I missed sharing my journey, and it’s always been something I loved.

So towards the end of the year, I thought about seriously rebranding my content. I started sharing my genuine love for food and fitness but framed it in a completely different, healthier way, and this was around the time when I’d just discovered Hyrox.

A lot of people knew I was into running and marathons, but what really drew me to this sport was that I could build my body in a way that felt most natural to me - develop strength in both my upper and lower body without having to drop weight, lose my period, or risk the injuries that often come with trying to reach elite marathon times. Training for Hyrox lets me be strong and fast, not one at the expense of the other, and I was super excited to share this with others.

Don’t get me wrong, rebranding online isn’t easy 😬 But so far, I’m having the best time sharing my fitness journey and everything I’m learning. Plus, when I announced my big goal to become an Elite 15 Hyrox athlete on Instagram recently, the response was genuinely overwhelming in the best way possible - something I really didn’t expect.

(Here’s the post if you want to check it out.)

You told me you are excited and scared to make this leap. That resonates so much. Tell me about that tension?

I’m incredibly excited because the upsides are pretty much limitless. I have no idea where this path will take me, how far I can take my fitness in Hyrox, or where I’ll be in say 3-5 years’ time.

But that uncertainty is what also makes me somewhat scared. What if things don’t work out? What if my savings dry up and I’m not yet making any money to support my life? What if I get a major injury? What if I don’t make as much progress as I think?

I can often think very catastrophically and worry too much about the “what ifs” so I’m working on trying to limit these thoughts and feelings. I’m also trying to turn these negatives into something more hopeful. In particular, I’m reminding myself that any failures are simply learnings. Even if I don’t make the Elite 15, I’ll have spent years doing something I genuinely love, becoming the strongest and healthiest version of myself, and living a life designed around my values rather than someone else’s - and to me, that’s totally worth the risk.

How much of a role was your partner deciding to quit with you in deciding to take this leap? How did you talk about the tradeoffs in the decision?

Funny story here actually: Angelo and I met on Hinge (2022) after he stumbled across one of my photos from my first ever London Marathon. We clicked pretty much straight away, and in particular, we both shared this huge love for running, fitness, and becoming the healthiest versions of ourselves.

Fast forward to 2025 and we bought a flat together in London. It was something we’d been wanting to do for a while, and we honestly thought we’d “made it” as real adults. We both had stable jobs, stable incomes, and started building the routines that we’d always talked about - run at optimal times in nice parks, go to the gym, meal prep on Sundays, stuff like that.

We genuinely thought this was it. So it makes me laugh now that only 8 months later we were looking for tenants, purchasing a 150L backpack, and getting ready to leave the country altogether 😂

I know a lot of people think we’re absolutely crazy. Like, why the hell would we give up decent jobs, a mortgage, and a life we’d spent years working towards? It just doesn’t seem to make sense.

But the thing is, sometimes you have to walk through one door in life to realise it’s not quite right for you. Sure, it would’ve been great to realise that we wanted to become elite athletes before we bought a property, but life doesn’t quite work like that.

And I guess the question is: what actually changed? And why did we change our minds?

Well, when Angelo and I started living together, we started watching more and more content online about this new and interesting sport called Hyrox. We watched races, got completely hooked, and of course, almost immediately signed up to our first one. As we were putting more and more hours into our training, we started to realise we were capped. We were working out too late, eating even later, missing sleep, recovery was suffering … and we started craving more and more time for this one thing we loved most.

At the same time, Ali was talking more and more about financial freedom and building a lifestyle business, and as his copywriter, I was literally absorbing everything he was saying and learning. Oh and I also read your book, Good Work, which made me see work in a completely new light.

So one day - I can’t remember when exactly - we dabbled with the idea of dedicating our lives to fitness. We thought about starting a business, coaching, or building an app, but then we were eventually like, why don’t we prioritise our own fitness first and then document the journey?

I’ll be totally honest here and say we hadn’t even done our first Hyrox race yet, which definitely makes us crazy, but we were so determined that with hard work and consistency, we could get to the top. And I guess only time (and a lot of hard work and sweat) will tell.

But we’re on this journey together, we have each other’s backs, and it’s the most incredible thing to be chasing your dreams with your best friend and the person you love.

What’s the plan? Where can we follow you?

Right now, the plan is to really dial in my own training and aim for the Elite 15 in Hyrox. Simple on paper, but most likely a lot harder in practice 😅

That’s my ultimate goal, but even if I don’t ever end up “making it”, I’m trying to build something sustainable alongside - long-term athlete or brand partnerships, potentially coaching if that feels like “good work” to me, and content creation that actually aligns with what I love. My athletic performance is definitely going to be the foundation, but there’s a whole ecosystem I can build around it and that’s what makes this whole thing feel less risky.

I’m currently sharing my journey, tips, and advice over on Instagram (@byhollygabrielle) where I’m active most days, and Angelo and I have started a new YouTube channel together (@angeloandholly). We’re posting one video a week to share our training, racing, and the reality of this whole journey.

Oh and we’re also travelling around and living in more affordable cities compared to London to make our savings go a little bit further. I always thought I’d be a “home” person who loves stability, but I actually don’t. I love the idea of exploring new places and building homes across the world, and I feel super lucky to do this.

Hey there! I’m still on sabbatical, but I hope you enjoyed this issue

I’ve been doing some form of public writing since 2015. I’ve somehow figured out how to hack a living doing things like writing books and launching premium art editions of my book. If you like what you read here, you’ll probably enjoy my books The Pathless Path and Good Work:

If you’d like to join a virtual community of others on “pathless paths” from around the world, and get access to courses, tools, and other resources I’ve created over the years, you can join The Pathless Path Community. Our recent WhatsApp community is very active if you like hanging out on messaging apps instead of Circle.

Some things I endorse:

• Readwise is offering 2 months free (I use it for book notes and reviewing highlights). Or two months free on

• Readwise Reader, which I use for RSS reading and epub reading

• Crowdhealth, an alternative to US health insurance that I’m still using while abroad

• Postbridge: A social scheduling app created by a reader without crazy upcharges for more accounts

• Kindred, a home-sharing app

• Collective for handling your S-Corp accounting needs, and Nat Eliason’s Build Your Own AI Apps course

If you received this and find yourself in a state of outrage, thinking, “What is this?” I strongly encourage you to unsubscribe below. It is your God-given right, and there is plenty of other good stuff online.

A reminder: I don’t check unsubscribe alerts and never look at my subscriber list. So if you feel like unsubscribing, you can do so below.

If you haven’t filled out the reader survey, that would be a huge help:

Start Survey

(or survey here if you don’t have a Substack account)

I really enjoyed ’s book Unhinged Habits, and I’m happily writing a short post to promote it.

Too many books in this space are trying to be Deep Work or Atomic Habits. Despite using “habits,” I am grateful he did not attempt that playbook.

Some quick thoughts:

1. It was refreshingly honest: he keeps telling the reader about his experiments, successes, and failures in a down-to-earth, honest way. He didn’t seem to make any attempt at “selling” his own journey or story to make himself look impressive, nor did he try to package his life reflections into a neat framework. I liked it.

2. He shares unique perspectives and ideas he has actually tested and used in his life. Like me, he’s done many time-consuming and costly experiments on how he’s living his life. He’s made many mistakes. But that also makes his approaches useful because they are working. His 8:4 seasonal on-season/off-season approach is my favorite idea from the book (more on this below).

3. He shows the tradeoffs: Most “be successful” books are not that useful once you’ve read a few. Tactics are easy to figure out. But the tradeoffs? That’s where all the interesting ideas about the art of living are found. He has young children and other interests and preferences that take him away from work and success at this point in his journey. People may dismiss him because he’s already “made it” to some degree, but that didn’t bother me at all. Most of the interesting tradeoffs are not about money at a certain point. They are about deeper human desires like belonging, identity, and dignity. I connected with his journey of grappling with these.

4. Real personal stories: He weaved in two personal stories uniquely, as interludes to the chapters, that worked incredibly well. This made the book for me because when I finished it was like I read a good book, not just some playbook I had to feel guilty about not implementing.

YMMV, but if you liked The Pathless Path, you’ll likely enjoy this one too.

My high-level take on the book: I think Jonathan did a great job questioning the assumptions of the productivity/hustle complex and actually shows how he’s transcended many of those dynamics in his own life. Jonathan has been semi-nomadic with a family for many years and has also done the author/creator/entrepreneur thing for longer than me so the book was especially useful for me in terms of questioning and challenging a lot of my own ideas. 

The book took a little to get into, but I ended up finishing it quickly after getting into a flow. The book had its own unique structure which was really well executed with several personal interludes that made the story much more than a traditional self-help book.

Here are two ideas I’ve been thinking a lot about since:

Idea #1: The value of highly inefficient life tinkering

There’s a part where Jonathan talks about outsourcing the work to buying a bike. It’s not a major priority for him, so he lets someone else decide on the bike for him. I was expecting it to go smoothly and for him to espouse the benefits of optimizing your time. But then, he says, “the bike sucked.”

It made me laugh because I am constantly running similar experiments, often resulting in wasted time and money or finding myself in situations with unforeseen downsides.

I’ve come to see these experiences as a blessing. Earlier in my life, I was surface-level efficient, trying to manage the world. I avoided moving in uncomfortable directions because it was easier on a day-to-day basis. Now I know that the right amount of discomfort is not zero. I build inefficiency into my life. While sometimes it is annoying, it helps me be more effective in terms of constantly aligning and moving toward the life I actually want.

From Jonathan:

“There’s this old saying that goes “the unlived life is not worth living.” Well, an overly productive life is not worth living, either. But the unbalanced life . . . the 8:4 life . . . is absolutely worth living. Because the unbalanced life is full of meaningful work, serendipity, exploration, and wonder.”

I agree.

Idea #2 The 8:4 season/off-season approach

My favorite part of the book was his 8:4 framework for seasonal living. He takes 8 months of the year when he’s “on season” and then four months when he’s in an “off season.” For him, his off-season is when he and his family live abroad, homeschool their kids, and spend more time as a family.

This is something I’ve been thinking a lot about since becoming a parent: Is there a way to live seasonally like this instead of trying to have it all? When I try to be excellent at work, parenting, health, and my relationships at the same time, I end up feeling like I’m dropping the ball on everything.

I’ve been thinking a lot about moving toward a more seasonal approach while my daughter is young, and the book was helpful, mostly because Jonathan has been A/B testing this for years.

Here’s an example when he’s in writing mode:

I’m in a season of writing. It’s three months long. I hope to mostly fin-ish the first draft of this book.

⁠⁠Four mornings a week, I wake up early to write for two hours. Before bed, I review my notes and plan the next day’s writing. Three days a week (Mondays, Thursdays, and Fridays) my entire work day is dedicated to this book. I have no meetings, no phone calls, and I don’t respond to emails.

When he’s in an off season, he creates a checklist of maintenance tasks he needs to keep up with. For example, shipping a newsletter once a week, doing financial reports, fitness, and payroll for his team.

For some reason, this reframing around “maintenance tasks” really clicked for me. It made me realize that I’ve kind of been in a never-ending offseason, always in maintenance mode, never really designing any “on-season” periods.

Inspired by the book, I decided to formally embrace off-season mode and take a more formal work sabbatical from January 15th to March 1st.

One thing the book spurred me to do was an audit of my “projects” in progress, and seeing it visually confirmed how many things I’m passively managing.

I started charting out a plan for this mini-sabbatical:

For this upcoming period, I drafted some very clear priorities:

Off-season priorities:

• Enjoy the traveling village community and time with Angie and my daughter

• Trying to experiment with dealing with some long-term health issues that are lingering

Off-season maintenance tasks:

• Check email once or twice a week in a dedicated block of time

• Help Angie with any tasks needed to help launch her book in March

• (Optional): Publish guest posts from others if needed

• Reply to the one contractor helping me with a small project as needed

At the end, I’ll start adding things back, reflect on what I’ve learned, and start tinkering (inefficiently, of course) with what a more seasonal approach to life might look like.

For me, this sabbatical is exciting. It’s also me walking the walk of my own advice, I often give of “doing less on the problem.”

I may post some guest posts people are working on (submissions of fully finished posts are welcome) or a quick reflection on the traveling village, but otherwise, see you in March!

Free Copies of Unhinged Habits - I’m doing a drawing and giving away copies of Unhinged Habits in my community. If you are in there, check out the WhatsApp community announcements for the link.

Check out the book

Hey there! I’m still on sabbatical, but I hope you enjoyed this issue

I’ve been doing some form of public writing since 2015. I’ve somehow figured out how to hack a living doing things like writing books and launching premium art editions of my book. If you like what you read here, you’ll probably enjoy my books The Pathless Path and Good Work:

If you’d like to join a virtual community of others on “pathless paths” from around the world, and get access to courses, tools, and other resources I’ve created over the years, you can join The Pathless Path Community. Our recent WhatsApp community is very active if you like hanging out on messaging apps instead of Circle.

Some things I endorse:

• Readwise is offering 2 months free (I use it for book notes and reviewing highlights). Or two months free on

• Readwise Reader, which I use for RSS reading and epub reading

• Crowdhealth, an alternative to US health insurance that I’m still using while abroad

• Postbridge: A social scheduling app created by a reader without crazy upcharges for more accounts

• Kindred, a home-sharing app

• Collective for handling your S-Corp accounting needs, and Nat Eliason’s Build Your Own AI Apps course

If you received this and find yourself in a state of outrage, thinking, “What is this?” I strongly encourage you to unsubscribe below. It is your God-given right, and there is plenty of other good stuff online.

A reminder: I don’t check unsubscribe alerts and never look at my subscriber list. So if you feel like unsubscribing, you can do so below.

If you haven’t filled out the reader survey, that would be a huge help:

Start Survey

(or survey here if you don’t have a Substack account)

A reader sent me these questions and gave me permission to share them

Reader is a 25-years old who has always been a winner on her default path. Working on Wall Street but feeling deeply unfulfilled and thinking about exploring a career break.

#1 Have you ever regretted not stepping onto the pathless path earlier than you did? As someone who just turned 25 and only had 3.5 years of experience working full-time in a big global company, I wonder if this is too early for me to go on this path.

It’s so hard to actually consider rewinding the clock. I think I wish I had stayed at McKinsey longer. To me, it was a mistake to leave so quickly to go get an MBA when I was 25. That was pure prestige goggles, and the just a general restlessness to keep moving. It was such a great place to work, and I had a clear path with supportive managers to move into more challenging roles. I also had many good friends there. ‘

I got swept up in everyone around me applying for MBA and other grad programs. I think for me, a big part of this was just scarcity mindsey. I felt like I had snuck into McKinsey and wasn’t like the other people working there. I had an urgency to capitalize on my opportunities.

But by doing this, I ended up sort of adrift for the next 7 years, bouncing from one consulting firm to another. Also, that clear path for growth never happened again. I had an absurdly bad stretch of bad luck, ending up in three consecutive positions where the senior person in my department quit before I started.

In my final job, I worked with a partner who really challenged me and pushed me to work more independently and directly with clients. I gained a lot of confidence in that role, and it helped me feel like I could sell freelance projects on my own but that job had a lot of other issues, and I probably led to a lot of burnout and resentment that I spent years recovering from.

Despite these missteps, I was still learning a bunch of random things by moving jobs, shifting my focus over time, learning on my own, and doing stuff beyond work. Even though I certainly still learn and grow on my own, I do sometimes miss the structure of a workweek, deliverables, and good teammates pushing me to do better.

But the regret is less about staying so long and more that I stayed too long on a path with clearly declining motivation over time. Jumping from job to job helped increase short-run motivation and learning every time I leapt, but the trend was not in a good direction.

So the question is instead: Are you in the flow of tasks and activities where your energy and interest level are at least steady or growing? If not, what actions might you have to take to move closer to such a path?

It might be worth thinking less in years before you are “ready” than looking at the next job/gig/step as one that hopefully pushes you and challenges you in a way you are already wanting to get better. What are the jobs, places, or gigs you could pursue that would increase your odds of being on a path where you are progressing in the way you want to progress? I think there are many new kinds of jobs in this emergent hybrid economy between normal jobs and the creator economy that are really great places to work. Working for top creators, talent agencies, in social media, and startups can give you access to feedback on increasingly valuable skills.

I think stepping back, you likely need some story to make sense of it, and also some sense of what you are hoping to gain. I’ve called this “leap capital” recently, or the story you are telling yourself that helps you make sense of your transition. Is it a “one-year experiment” or is it a permanent leap? Big difference. And then, is this a way of testing out things you are already doing independently? Launching a creative experiment from scratch? Doubling down on something that’s working? Six months to goof off? It all depends. All can be fine for the right person.

Finally, other questions like:

• Financially, is it risky? If so, how could you derisk it?

• Emotionally, what might it cost you? Is that somehow potentially a way to grow in emotional capacity?

• What relationships will be worse because of it? Can you deal with that in the short term?

• Finally, is it reversible? Can you get back to where you are now?

Ultimately, I can’t tell you when it’s right for you. You need to decide what you are doing and why.

#2 Do you think you are lucky to have “succeeded” in the pathless path? Sometimes I see some comments online about taking a career break / quitting without the next job lined up, people talk about the risk of not being able to find a better job, and say it is not guaranteed everyone would thrive doing it.

You are projecting success onto me.

Others in my situation might feel like they are failing. Others might feel excellent.

Personally, I don’t really relate to the idea of “success” as much as you may not believe that.

One weird thing: I felt FAR better on this path almost immediately, and in the several years in which I was very much just breaking even without much intention to scale, grow, or make money.

Those positive feelings mostly came from the inner game of the pathless path - getting to know myself, my interests, my tradeoffs, my money insecurities, dancing and accepting fear and uncertainty and so on.

I spent the first few years of my path pushing the edges of this new kind of life and seeing what I might actually want to be doing. It was exciting. As soon as I started building my life around a creative practice, I found a life rhythm that felt good and sustainable and then the question was “how do I fund this?” I’ve been able to fund it for 8.5 years and I have some confidence I can keep it going for the next 2-3 years. After that? I’m not sure, but I’ll probably figure something out.

When I quit, I had nothing lined up. It was the first time I did that. It was scary, but it seemed like a better option than jumping from job to job like I did too many times in my twenties. Weirdly, it was not having a plan that enabled me to see how much running away from the present I was doing on my previous path. It forced me to see what I was actually doing, get to know myself, and start to figure out the tradeoffs that really matter.

Also, who cares about this:

“people talk about the risk of not being able to find a better job and say it is not guaranteed everyone would thrive doing it.”

So what. What do you think?

People have this weird tendency to make these broad claims like “well, everyone can’t do Y” to dismiss the possibility. It’s an uninteresting statement. So what? What if I say something like “Everyone can’t hit a tennis ball like Federer,” does that stop you from wanting to play tennis? No, of course not. Some things can be worth doing even if you don’t thrive. I certainly felt like I was fumbling around for the first couple of years there but never thought, damn, I should go back to my former path because I’ll feel less like a fool.

So what I am trying to tell you: I felt successful at the same time I felt like a fool. If there is a feeling I’d attach to success if you forced me, it would be contentment. Until I quit my job, I felt the opposite of that: restlessness.

For some people, they are totally fine with restlessness or just rank career success, steady incomes, money, and fitting in above that inner feeling of contentedness. I don’t, and I know that makes me weird. And poorer. That’s the thing: Every choice has a cost. What are you willing to pay?

We make a lot of tradeoffs that others would not be happy with. I only feel like I’m thriving because I am clear-sighted about the costs and benefits of the path for now and want to keep going.

Is that success? Who knows.

That’s for you to decide :-)

#3 Do you think you will ever go back to a full-time job anytime in the future? Do you think there could be a full-time job in the world that could be even better for you?

I don’t think I’d be open to 48 weeks of 5-day in-office employment. The good news is that there is a lot more dynamism in the labor economy now in terms of how companies are willing to work with people.

I think I could easily see myself in an ongoing part-time role for a company as an advisor, consultant, or something like that. I’ve built up a lot of skills that are probably useful to a lot of companies, but I’ve also learned how to structure different kinds of projects, gigs, and products in ways that don’t require in-person attendance to receive compensation. I don’t think money would make me want to work full-time again as long as I can hack together a modest living on a US salary.

But if our family changed our goals and decided it would be best for me to go pursue income to meet our needs, I would be the best positioned in the family to go earn money, so I’d do it.

But Angie is not pushing me to go to work and enjoys my flexibility as much as I do!

How important is it to have met your wife and have her company in your journey?

Very important.

We never really separated for more than a month after we met. She’s been with me from the early days, and we’ve been co-building this life together. I think my journey would have been a lot harder without her. In many moments of doubt, I felt normal because she was on a similar path.

I talk to a lot of people who say things like “how do you convince your partner to be on board with a different kind of life or path?”

I have no idea. I married a weirdo.

Hey there! I’m still on sabbatical, but I hope you enjoyed this issue

I’ve been doing some form of public writing since 2015. I’ve somehow figured out how to hack a living doing things like writing books and launching premium art editions of my book. If you like what you read here, you’ll probably enjoy my books The Pathless Path and Good Work:

If you’d like to join a virtual community of others on “pathless paths” from around the world, and get access to courses, tools, and other resources I’ve created over the years, you can join The Pathless Path Community. Our recent WhatsApp community is very active if you like hanging out on messaging apps instead of Circle.

Some things I endorse:

• Readwise is offering 2 months free (I use it for book notes and reviewing highlights). Or two months free on

• Readwise Reader, which I use for RSS reading and epub reading

• Crowdhealth, an alternative to US health insurance that I’m still using while abroad

• Postbridge: A social scheduling app created by a reader without crazy upcharges for more accounts

• Kindred, a home-sharing app

• Collective for handling your S-Corp accounting needs, and Nat Eliason’s Build Your Own AI Apps course

If you received this and find yourself in a state of outrage, thinking, “What is this?” I strongly encourage you to unsubscribe below. It is your God-given right, and there is plenty of other good stuff online.

A reminder: I don’t check unsubscribe alerts and never look at my subscriber list. So if you feel like unsubscribing, you can do so below.

How To Leave The “Casino”

There is a lot written on how to build a startup, but not enough written on how to build a solopreneur business. My go-to book for years has been ’s Art of Gig series, but his writing can be a bit challenging for beginners (these books are still in my must read category if you are committed to an indie path for more than a year).

Luckily, ’s new book and workbook, Leaving the Casino, offers an absurdly useful guide on how to think through building a business on your own. What made it great, something I’m excited to recommend, is that it goes beyond tactics and pushes people to think through prompts, frameworks, and a well-thought-out process to go much deeper, focusing on the foundation level of your business.

It’s also pretty funny as she pokes fun of what she calls the “Entrepreneurial Casino”:

The Entrepreneurial Casino is a multibillion-dollar industry built around the dream of entrepreneurship, focused on selling quick and easy solutions to grow your fame and fortune. The influencers selling you these solutions are experts at using every marketing tactic in the book to ensnare you—scarcity, urgency, social proof, even sex appeal. It’s the course-based version of diet pills: fast promises of big results with little effort. This makes the tech platforms the ultimate winners of this game—you pay big bucks to advertise while your attention and data are commoditized and sold to the highest bidder.

…

And when their strategies didn’t work? I was told to try again. Just invest a little more. Take the next course, upgrade to the premium mastermind, “fix my mindset,” and the oasis of success would finally be within reach.

And she goes on:

Because I’ve had such a variety of experiences—engineering, consulting, big corporate businesses, the startup world, and building my own business (first as a life coach and then as a fractional COO)—I can see across all of the different floors of the Casino.

The boss babes and manifestation girlies on Instagram showing off their luxury lifestyles.

The Twitter/X and YouTube bros promising that you can have six-figure revenue months just by writing content for one hour a day.

The B2B marketers turning LinkedIn into a sea of homogenized and flattened expertise that always leads with a “hook.” (Feels like a hook, line, and sinker to me.)

But I can use my experience to curate what does work in business and turn a torrential sea of information and shoddy promises into frameworks and tools specifically designed for small, knowledge-based businesses (like the ones I’ve built myself). The skills I honed in corporate strategy—diagnosing systems, analyzing trade-offs, and building sustainable solutions—are the same tools that can be applied to help entrepreneurs create profitable and sustainable businesses without sacrificing their values or well-being.

I have felt many of the same things and it’s not a coincidence that we both spent time working in strategy consulting before exploring an indie path.

A lot of people like to dunk on consulting but the best part of the experience was being exposed to hundreds of different global businesses and seeing how businesses actually make money. On top of that, we both DID ultimately leave consulting because sometimes it does get caught up in buzzwords, fads, and doesn’t quite deliver.

So I asked Jessica to do a little Q&A for us.

Without further ado, I’m handing it over to her:

The metaphor of the “casino” for the modern state of advice around doing your own thing made me laugh. When did you first come up with this idea?

I left my full-time job in March 2021, and I did contract consulting work while building my own book of business. Later that year, I wanted to grow faster, so I did what “everyone” was doing—I joined a $25,000 mastermind, because in the silo of the online business ecosystem I was in, that was the common step at that point in time.

I could cashflow it from corporate savings (ex-McKinsey, ex-Nike) and my contract work. But I got in the room and looked around—and at least 12 of the other 14 people had no substantial business. I’m thinking: How are they paying for this? And also: Are they even paying full price? Because I was, and I felt like the sucker who pays full freight at a Vegas hotel, while everyone else got their room and drinks comped.

Then we started talking about marketing. At this point, I was building a fractional COO service, and the advice was all about email funnels, social media launches, cohort-style selling. I’m recognizing: This doesn’t fit my business model at all. Nor does it fit theirs, based on their stage of business.

That’s when I asked myself: Who’s really making money here?

Because the person leading the group was making multiple six figures, from people who had no business paying for that level of support.

And I thought, “Of course. The house always wins.”

Once I had that metaphor, everything clicked. What people were being taught wasn’t business building—it was gambling. Spin the wheel on a high-ticket program. Keep pulling the slot machine of social media posting, and hope you go viral.

A few lucky people win big (often due to pre-existing advantages, market timing, or platform arbitrage), and everyone else loses their money.

The hook: “Make six figures from just doing an hour of deep work every day!”

The reality: “Make six figures by getting on Twitter at its peak (and YouTube seven years ago) and build an audience teaching people how to make six figures from an hour of deep work a day!”

I think you do a great job of painting the picture of what a solopreneur path requires. I don’t think there’s been enough written about all the tradeoffs you constantly need to make, and also the variety of tools and content decisions you need to be making in the modern world.

Talking about trade-offs invites nuance. And the entrepreneurial casino is designed to make you stop thinking about trade-offs and just dangle support.

When I tell people it’s going to take two to three years of effort, probably at a minimum, to build back up to their corporate salary, few people want to hear it. One, because that’s not sexy. Two, because many people don’t have that kind of cash saved up to bridge the gap.

So to get the broadest audience, you must sell the dream.

And early on, I believed that if you talk about the trade-offs, no one buys from you.

Gain a lot of followers to have “influence”? You might end up resenting talking about the same topic on a relentless publishing schedule for years.

Build an agency so you can have your team deliver while you’re the CEO? Most agency owners I know make less take home than profitable soloists because of the costs of running their team.

Every path requires the time and effort to walk it, which isn’t an easy sell, especially to newer entrepreneurs who want hope and clear next steps.

I love Paul’s writing because he’s so honest and talks about the tradeoffs. To do entrepreneurship with a high level of creative autonomy and flexibility means his business is less financially lucrative than it could otherwise be.

I wrote this book because I couldn’t find one that articulates the practicalities of how to navigate those trade-offs for expert-led businesses. Many books are memoir mixed with “this is how I did it” to help fuel a speaking career. Mine is meant to be “here’s everything you won’t get from an MBA that I’ve learned from tens of thousands of dollars in programs and years of pattern-matching”.

You seem to find a good balance between engaging in content and sharing online and mostly focusing on your business behind the scenes. I think people who want to work independently feel like they need to be doing social media but that’s not quite true (it’s just the loudest voices telling us that). What forms of content have worked well for you and feel sustainable?

For my business to be successful early on, I didn’t need thousands of followers. I needed five clients.

And replicating what I saw from working at McKinsey, they weren’t posting on social media every day to get clients. They were doing traditional business development—tapping networks, building relationships, building authority through long-form asset creation.

So that’s what I did.

My content strategy is the codification of patterns I’ve seen or topics I want to explore with my clients next.

Every week I write a long-form newsletter.

Every month for three years I taught a free class (not a sales pitch webinar, an actual free business building class). Those classes and long-form content ended up laddering into the book.

And then I guested on other people’s podcasts and guest taught in other communities, because of those relationships I’d built and the frameworks I’d developed.

I’m terrible at anything that requires algorithmic discoverability, like short-form video or tweets/Notes. What I lack in performance, I make up for in relentless consistency.

Now, as I’m moving into more visibility with the book, I need more eyeballs on my work. But in order for me to make money when I started, I didn’t need to have a ton of followers. I needed to have 50 solid relationships.

How long did it take you at the start of your journey to find your footing and have the feeling like “ah, okay, I have confidence that I want to stay on this path”?

I knew immediately I never wanted to go back to corporate. But wanting to stay on the path and having confidence in the path are two different things.

The first two and a half years? I was running from something—toxic corporate environments, doing two jobs with the salary and time of one, poor leadership decisions I could see from a mile away. I hated every moment of the corporate theater shenanigans where I had to spend more time prepping absent leadership for meetings than making decisions.

So I did contract consulting and fractional COO work to pay the bills while building my own book of business on the side.

Around year three, something shifted. I realized the business skills I’d learned at McKinsey and Nike—the ones that made my financial success faster than most soloists—weren’t being taught anywhere. That’s when I moved from running from corporate to running toward something: teaching the foundations that actually work.

It’s taken me five years to feel like I have solid momentum and can take the foot off of the gas a bit related to my pace. Now that the book is in the world, it’s an asset that people can really share that has already started to bring in new people to my world.

You also come from a consulting background, working at McKinsey for several years. For me, experience at McKinsey was invaluable prep for working on my own, but not for the reasons people think. For me, the value was being part of a well-run organization where I could get tons of reps, aiming at a high-quality bar, working at a fast pace, and where everyone around me was always pushing me to do better. I don’t think I could have written a book on my own without this. What stands out from consulting for you?

I couldn’t have written the book without McKinsey. And I couldn’t have run my business without Nike.

McKinsey taught me how to pattern match quickly, how to get to root causes, how to architect my business experiments with an hypothesis-led approach. It taught me to think in frameworks. When you start thinking in slides—when everything has to be bucketized, structured, framed—that shapes how you communicate.

My signature framework—what business are you running—only exists because McKinsey taught me MECE (mutually exclusive, collectively exhaustive). I had to see that this person’s business is fundamentally different from that one, but both are distinct from this third one. Bucketizing and creating coherent structures is pure McKinsey training.

But running my business? That’s Nike.

McKinsey teaches you one pace: on. Full sprint, all the time. Which is why I left after 3 years because the pace was just too intense for me.

Nike taught me rhythms. I worked in planning and inventory management for five years, and you’re thinking in multiple horizons simultaneously. What’s coming from global design three years from now, and how does that information affect what I need to buy based on what I’m liquidating right now?

Nike gave me the rhythms of repeatability. Every season, we ran the same playbook of dates, gates, stages. Every month, similar processes for reviewing results. Those rhythms were ingrained in me through years of leading sales and operations planning processes.

McKinsey taught me how to think. Nike taught me how to operate.

One side effect: my course slides are very dense. At McKinsey, your slides had to be your entire talk track—just put in slide format. My slides still work that way, incredibly dense with all of my thinking on the slides.

You go pretty hard against the promise of passive income, which I think makes sense given how much it’s oversold to people. However, now you have a book in which you will earn income…passively. I’ve come to reframe this as “less than grind” income, or LTG income, meaning its less energy than a job to maintain but still requires maintenance. How do you think about this now that readers of this newsletter are about to purchase your book and send money to your bank account while you sleep :-)

I like your reframe—”less than grind.” I call it leverage.

Now that I’ve done years of learning and years of writing and teaching, it’s much more effective for all of us if I codify that into a single artifact you can consume at your own time and pace, instead of you having to buy my time to share that information.

Readers get a painstakingly crafted book, or buy my membership and get a curated curriculum and set of tools, and know that it’s the best I could make it instead of the best based on how I explain the concept during their call. I want people to spend their time and money on implementation, not just information.

Sure, I’ll have purchases come in while I’m asleep. But what people may not know are the years I’ve spent building a relationship with Paul, supporting and sharing his work, making sure I met him IRL when we were at the same conference, gifting him the book before it came out, etc. Over five years of relationship building which has culminated in Paul trusting me enough to read my book, recommend it, and letting me share this with his readers.

Nothing about that approach is passive. 🙂

Of course, I still make the money I need to fund my life through maintaining an active roster of consulting clients and cohort members—which isn’t passive either.

Who are some underappreciated voices for engaging on these kinds of paths that people may not have heard of?

My favorite two underappreciated voices are Lex Roman and . Lex runs Revenue Rulebreaker, a newsletter and membership collective devoted to publishing the rulebreaking revenue stories of solopreneurs and fostering indie business collaboration. Amelia Hruby runs Softer Sounds, a podcast production studio and Off the Grid, a podcast, book and community dedicated to a vision of the internet where we create, connect & make money online without extractive algorithms.

Okay Paul here again. Please follow Jessica. She is a wise guide in the world of indie entrepreneurship. And purchase her book here.

Check out her book

Reader Survey - Help me share cool data next week?

I shared a link to a reader survey last week. It has some basic demographic questions, interest questions, and a couple of fun questions as well. I’ll share the results of next week in the newsletter.

Start Survey

Also, a few of you said you had trouble logging in to the Substack-hosted survey, so if you want to use a direct link, you can do that here.

#1 Write Once, Read Forever

Today I had a conversation with a reader here in Taipei who had only recently stumbled upon my writing, first discovering the Wise Agency series from last month, and then immediately reading The Pathless Path. It was interesting to talk to someone who had very little context on most of my journey and writing. He was appreciative of the Wise Agency remix of my ideas, even though I’ve been feeling like I’m rehashing the same ideas too much.

It’s a good reminder that my desire to always ship something new, novel, and inspiring is a hard and impossible bar for myself. It’s also why I’m playing with this new format, which is mostly what the newsletter was from 2017 to 2019.

I want to ship interesting essays less frequently and dedicate more time to book-length projects than to medium-length newsletter essays.

We’ll see how it goes!

#2 Some Things I Read & Enjoyed

• ’s book Leaving the Casino is an excellent guide for new indie freelancers who want to build their own solopreneur business but want more substance than the traditional tactic-style advice found online

• I finished The Other Side of Change by . This is a book of stories about people who went through changes in their lives. If you like the kind of reporting style non-fiction books that interweave a bunch of stories about people, you’ll like this book. The writing is down-to-earth, and it doesn’t come with an agenda of any kind. The best part, by far, was the final chapter in which Maya detailed her own challenges trying to build a family, which, given some of our own recent challenges, was relatable and powerful.

• And I also finished Unhinged Habits by . This was GREAT. I loved it so much that I am going to be writing about it next week. I think this will be a great companion for people on a pathless path who can’t quite commit to one thing or one habit forever.

• Vitalik’s essay on popup cities and other experiments in living is very good:

But I also think there is something different at play: people just have to get off their butts and actually create these alternative cultures and environments, and doing it is hard. Startups are also hard. But startups have had a multi-billion-pdollar capitalist optimization machine figuring out all the most optimized ways of doing them and rapidly growing them to scale, and turned them into cookie-cutter standardized playbooks. Culture does not have the same profit motive

• Also, 12 underrated reads from 2025:

#3 Books

just put the finishing touches on her memoir, Made in Taiwan. English translation will be out later this year.

However, if you read traditional Chinese and would like to receive updates, please sign up for her newsletter or express your interest here.

#4 People/Things Worth Following

and new podcast Small Creator, Big World is a great one. Both share the perspective of creating while having full-time jobs in the creator world. I love the frame of a “small creator” and have a video coming out about it, too. They both have great chemistry together, and I’m lucky they are friends too:

Small Creator Big World

A podcast for small creators with big dreams

By Becky Isjwara

#5 A Tweet

I don’t know how the age of AI will change work narratives, but you can already feel it shifting.

Give me more data to analyze by filling out the reader survey before you go

I shared a link to a reader survey last week. It has some basic demographic questions, interest questions, and a couple of fun questions as well. I’ll share the results of next week in the newsletter.

Start Survey (with substack account)

Start Survey (no substack account)

Paul finally wrote a shorter issue, nice

Short for me at least.

I’ve been doing some form of public writing since 2015. I’ve somehow figured out how to hack a living doing things like writing books and launching premium art editions of my book. If you like what you read here, you’ll probably enjoy my books The Pathless Path and Good Work:

If you’d like to join a virtual community of others on “pathless paths” from around the world, and get access to courses, tools, and other resources I’ve created over the years, you can join The Pathless Path Community. Our recent WhatsApp community is very active if you like hanging out on messaging apps instead of Circle.

Some things I endorse:

• Readwise is offering 2 months free (I use it for book notes and reviewing highlights). Or two months free on

• Readwise Reader, which I use for RSS reading and epub reading

• Crowdhealth, an alternative to US health insurance that I’m still using while abroad

• Postbridge: A social scheduling app created by a reader without crazy upcharges for more accounts

• Kindred, a home-sharing app

• Collective for handling your S-Corp accounting needs, and Nat Eliason’s Build Your Own AI Apps course

If you received this and find yourself in a state of outrage, thinking, “What is this?” I strongly encourage you to unsubscribe below. It is your God-given right, and there is plenty of other good stuff online.

A reminder: I don’t check unsubscribe alerts and never look at my subscriber list. So if you feel like unsubscribing, you can do so below.

Please fill out the Pathless reader survey:

I’m doing a survey of Pathless readers as I rethink my approach for 2026. Expect more experiments, different formats, and more investment in my community over the next year.

Take The Reader Survey (5 Mins)

Reflecting on 2025

For the eighth time, I accomplished my only real goal: don’t go back to the paycheck world.

The reality is that this year felt like a year of treading water on the business front. I kept feeling a bit stuck, trying to find my way out before concluding at the end of the year that my priorities weren’t really to crush it on the work front anyway. My priorities for the year were:

1. Being a dad

2. Supporting Angie and helping her finish her book, Made in Taiwan

3. My hardcover book launch

4. All the other stuff

I spent too much time worrying about #4 and not giving myself credit for doing quite well on #1-3.

#1 Wrote a bunch of stuff

I spent lots of time tinkering with AI tools, contemplated my relationship with creating and sharing ideas, poked fun at the hustle bros, celebrated my eight pathless anniversary, shared 40 lessons on learning 40, riffed on AI & Work, explored rabbit holes like protocols and seapunk, launched my biggest project, the premium hardcover, and riffed on “wise agency” after giving a talk on the subject.

Looking at these posts from the year, I have a couple of thoughts

• Yes, I was all over the place

• I was a bit more generative and creative than I thought

Behind the scenes, I dabbled and wrote quite a bit in a few book drafts. Those books didn’t really find flow toward a finishing point, but I intend to revisit them in 2026 and see if we can ship 1-2 of them and/or experiment with new ways of producing and publishing books and mini-books.

As always, the goal remains: “write most days.”

#2 Did some podcasts

I published 13 podcast episodes, and 3 of these were me being interviewed on other podcasts. It’s clear, I can’t quite sustain the podcast right now, and I’ll still post episodes here and there, but don’t expect to spend much time on it in 2025.

Some of my favorite episodes this year include the convo with Nat Eliason on writing books, Steven Foster on his pathless path and living in Idaho, Andrew Taggart on The Yoga of Work, Pranab Sachi on “attentional co-piloting”, and Dennis Owen on The Art of Retirement.

#3 Business Kept Operating

Behind the scenes, my businesses kept humming. Most income flows are down year-over-year, but still enough to fund my life. People kept buying The Pathless Path, and my consulting skills course seems to still have a market despite declining over the past couple of years. I also did a few corporate workshops, which helped my confidence throughout the year. I plan to share more, but here is a high-level picture of the year:

Most of my income and profit came in the fourth quarter from sales of the hardcover and black friday sales from my consulting course. This was the first year I was in a bit of a panic financially in terms of needing new sources of revenue, but it feels good to finish the year solidly in the black, earning about $10-15k more than our cost of living.

My margins were about 43% this year, but if I subtract out the hardcover investment, they were closer to 70%.

I’m looking forward to getting back to running a leaner and more profitable operation next year.

Here are some reflections earlier this year on my eighth! year in business:

#4 The Hardcover Feels Like A W

I’ve never made a big bet like this before, but for me it feels like a W already.

My modest mental goal was 100 books, and I ended up selling about 325 via 250 of the launch and premium buy-one-gift-one bundles. This generated about $35-40k in revenue, which paid off about half of the investment. I had a huge bill of $36k in November for the remainder of the printing costs for the notebooks and books, and it was nice to be able to pay for it with sales rather than have to dip into personal savings.

I was able to fully fund the investment from cash flows from the business, and my mental accounting is seeing this as a past sunk cost, meaning 2026, all sales will be cash flow positive.

This tested me mentally. I’ve never frontloaded money into a project at this scale, and it definitely stirred up some anxiety. I wrote a bit here, and if you didn’t read my essay on the “why,” you can check that out as well

#5 Expanding My Store

The direct sales experience has gone really well, and I’ve decided to expand the selections in my Shopify store. You can now purchase paperbacks, ebooks, notebooks, the pathless hat, and bulk copies of the premium hardcover directly from me.

My hunch is that direct sales will be a big part of making this author path work by producing one-off collectible items, offering bundles, and also signed books.

The premium hardcover bundles will continue to be available with gift wrapping, free notebooks, and illustration cards until I decide otherwise, but you can now buy the notebooks (which people really love and are nicer than you’d expect) on their own now:

Shop The Store

Still figuring out Shopify and such, so if you have any feedback, do let me know!

#6 The Community Is The Most Energizing It’s Been In Three Years

I launched a community in 2023, and the first year never quite worked with the monthly payment model (too much churn and admin work to handle it). Since shifting to a one-time fee, it has grown, attracted a vibrant group of people who are active in sharing and connecting with others, and it resulted in us shipping our first print project (via The Pathless Collective), not to mention many offline connections.

One big improvement was shifting away from Circle and to a WhatsApp community, which is about 10x more active and a medium I am better at engaging with.

It doesn’t make much money right now (about $4-5k in 2025) but it is something I find myself pulled to more these days. If you’d like to join us, one of the members is going to be hosting a deep reading group starting in January (will share more when I have it), and also hosts weekly serendipity sessions.

#7 Had so much fun being a dad

I’ve been thinking about the idea of “quantity not quality” when it comes to being a parent to a young child. This is mostly because when you’re with a young child, especially a 2-year old, the time is not “high quality,” its usually pure chaos. Yet the more time I spend with me daughter and the more time we spend together as a family when we are not rushed or stressed, the happier I am.

I feel so lucky to have a delightfully happy, silly, and fun daughter. I’ve had so much fun spending ton of time with her over the last 2+ years and its by far been the highlight of the past few years. I've become sillier, more playful, and happier despite many challenges on the health and work front.

Sometimes I feel like my path is a bit crazy and that eventually, its not going to work anymore. That may be true but I think I’ve been to stressed about it. My “compensation” for this way of approaching life has been tons of quantity time with my daughter. And I wouldn’t sell it for anything.

#8 Taking Some Time off At The Beginning of 2026

I’ve taken half-action on too many small things over the last couple of years and am not finding forward momentum on enough things. Instead of trying harder, I’m going to take my own advice: “Have you tried doing less on the problem?”

We’re starting the year participating in a “Traveling village” with 20 other families in 3 different countries from January to May. I decided I’ll take a break from January 7th until the end of the first location, February 21st, and likely until the end of February.

I used to take “leisure weeks” every seventh week, and they really helped me both connect with what I’m deeply driven by AND take action/ship stuff. That’s fallen off since I finished Good Work in 2024, and I’m going to see how this mini-sabbatical goes.

Please fill out the Pathless reader survey:

I’m surveying Pathless readers as I rethink my approach for 2026. Expect more experiments, different formats, and more investment in my community over the next year.

Take The Reader Survey (5 Mins)

Finally, thank you!

You have no idea how grateful I am to people who engage with my work. The fact that this path is still going and I get to work on interesting things and spend my time in a way that feels good most days is remarkable.

If you aren’t getting what you want from my writing or work, though, please unsubscribe.

There is so much good stuff out there!

Order the Hardcover

This is part of the Wise Agency series. Click here for all three parts.

In the last post, I covered the period of “getting lost” and arriving home to “wise agency.” It’s a remix of past ideas I’ve written about, but in the context of an interesting 2x2 framework, with some fun visuals I created using Google’s latest image model. You can read the first two installments:

This post is a continuation of the “wise agency” part of the quadrant, which, for me, is just the beginning of acting in the world from a new perspective, a journey that basically will never end. In the last eight and a half years of this journey for me, I have not really moved past a feeling of “beginning again.” I suspect this never ends, in a good way.

More specifically, I wanted to focus on a few things that almost everyone struggles with and some useful ideas and frameworks that might help with:

1. What to work on

2. How to do it

3. When and how much to do it

Zooming out, these are pieces of a book that was never finished, something I was tentatively calling a “creator’s field guide,” something I’ve now chopped up into Good Work (published!) and Buy Your Freedom (publish date: TBD), and delivered in several workshops over the last year.

There’s a lot of interesting stuff in that draft that I want to share in some form, so I’ll likely be sprinkling it out via the Substack in 2026 or thinking of fun ways to launch it as a lower-lift book in digital form (if you have thoughts, let me know!)

First, how do you know what to work on?

One of the biggest fears people have about making a life transition: I don’t know what I’d do with my time.

Most people who do end up making a big change in their life either don’t have this fear or have said, screw it, I’m going to step into the unknown anyway.

They typically have one or two things going for them, too:

1. They’ve either been dabbling with projects, identities, or interests that don’t fit their current life, and they want to do more of them, or

2. They have reframed needing to be perfect at everything to seeing life as a series of experiments, most of which are allowed to fail

   1. Shoutout to who wins coined phrase of the year with “Tiny Experiments,” the title of her book, which lays out this shift

My spin on doing tiny experiments has been something I’ve called “Ship, Quit, and Learn.”

Since 2018, I’ve taken this approach with launching experiments, focused on three things:

1. What can I ship quickly?

2. What’s the off-ramp? How do I design it for quitting?

3. What does the experiment tell me about what to do next? (What did I learn)

This is the opposite of what many people think they should be doing.

Most of us grew up in a culture and schools that teach us a lesson we must unlearn: That we should always do our best to get an A on everything we do.

This is a bad approach if you are embarking on a new path because the goal is not to be universally successful, but to keep learning and evolving without re-creating the path you are moving away from.

The way to do this is to try lots of stuff.

Without this shift in aims, many people will re-create the same problems they just escaped because they are using the same strengths and tendencies as they did before.

The point of wisely acting in the world is to step into new terrain and to create new possibilities for living your life that you couldn’t quite access before. This requires embracing new emotions and new behaviors despite knowing there might be more productive and expedient ways forward

The thing I like about being self-employed is that I can try tons of stuff, somewhat without anyone noticing. When employed, a new experiment looks like a dramatic job change. Now, I can spin something up or shut it down quietly within a couple of days.

Here are dozens of the legible experiments I’ve tried over the past ten years, most of which have “failed”:

Beyond this, there are probably 100 other things I’ve thought about doing that I haven’t taken much action on. Usually, it’s because I’ve tested the thought with people and saw a lack of resonance, or I decide to wait a bit to see if I’m still excited about it. My recent hardcover book is an example of a project that I couldn’t stop thinking about.

Over the years, I’ve stolen a bunch of decision-making heuristics from others to help me make decisions and get better at starting and stopping various endeavors.

These six decision lenses help me look at things from different perspectives and override some of the more base impulses that drive us to chase various things:

1. If you knew it would fail, how would you approach it?

2. How excited are you on a scale of 1-10? You can’t pick 7. Only 8+ is a yes

3. Hell yeah or no. Simple.

4. How much would you pay for the opportunity to work on the project?

5. Is it a “full body yes”?

6. Am I deciding to be myself and follow what I want, or am I deciding to try to manage the future or a future projection of myself?

As an example, using question #4, I realized I’d pay $1,000 to avoid a project two years ago. This gave me the confidence to make a strong counteroffer on my terms, which turned the project into something I was excited to do and paid me twice as much money.

But many things, especially if they are new, novel, or weird, still require a leap of faith. No decision framework will ever give you perfect information. The goal on a path of wise agency is to be pushing the frontier of what you are currently capable of and what is slightly beyond that, all aligned with a growing intuitive sense of what is “right” for you.

has a great phrase here, “do the weirdest thing that feels right.” That’s what I’m talking about here.

This doesn’t stop people from wanting a playbook. Many people approach me now and ask how they can sell a lot of books. While I’ve written 7k words on my marketing efforts, I still would claim that I don’t fully know why anything worked.

All I could honestly say is do exactly what I did: Spend years on the wrong path, but developing tons of skills that will later help you be a good writer. Then quit. Decide to write more consistently after a year. Then, write without attempting to make money from writing for years without any goals. Talk to literally anyone who wants to talk to you about work, optimize your project selection and experiments around interest level and fun, and all along the way, live well below your means so you can keep buying time to keep going.

Oh.

Most people just want a magic book launch playbook.

The reality behind most people’s successes, if they are honestly willing to share it with you, will look messy like this:

This only “worked” for me because, along the way, I was enjoying what I was doing, getting better at selecting projects, and becoming wiser about a meta-game I was participating in.

As I was in the midst of all of these projects, I kept trying to make sense of my own game, learning about what was working, and trying to be honest with myself throughout. This tendency to sensemake my own path has resulted in many fun diagrams over the years.

From 2020:

2021:

2022:

None of these are perfect representations of my path. But all capture my attempts to play a long-term game without legible money or status goals as the priority.

I think one thing they do capture is the confusing state of going against the default games that most people are playing. I suspect that if you are also rejecting default aims, you must develop your own frameworks, sets of principles, and a good understanding of the trade-offs you are making.

Each time I write about what I’m doing or create a new framework, I am reality-checking my own internal storytelling and then exposing it to public criticism.

This has helped me remain honest with myself. If I were claiming success but were not financially viable or satisfied with the way things are going, what the hell am I doing?

Some people can’t tell a story that doesn’t align with how they show up. That inconsistency drives me nuts, so I use it to my advantage.

Second, how do we think about our relationship to the work?

Too many people try to fit themselves into existing paradigms on new paths.

They look at what other people are doing and think: I will do that!

Everyone is doing a Substack subscription, so I will do that!

Everyone is making money on Substack doing X. I must do that too!

This is a fine place to start if you are still learning about what works, but eventually, you need to move on to what works for you, for long periods of time, independent of outside forces.

This is really hard, but it is something you should almost always be thinking about. If you are someone who is going to take a shot at being an independent consultant, you should definitely have models of pricing, offerings, ways of working, and different styles. In fact, learning about the range of models is vital early on. But eventually, the point of the work needs to shift away from copying what works to you making choices that will help you naturally evolve into a style and way of working that only you can inhabit. You can probably map this to any sort of life mode beyond work, for example, parenting.

The reason copying other people is not wise is that you are not in a position to be adaptive. You are at the whims of a complex system that is on the edge of chaos and will keep changing.

A shift I encourage people to make is to Don’t Find a Niche, Find a Mode. As I wrote:

Find a mode where you can continue to be excited about what you are doing.

Find a mode where the friction to getting started declines over time.

Find a mode where you are excited to keep going despite being ignored.

Find a mode where you want to do something despite not having anything to show for it or in the worst case, despite criticism.

After I quit my job, my niche goggles made it very obvious that I could morph myself into a character in the LinkedIn corporate thought leader space. There are lots of legible opportunities, speaking gigs, consulting projects, and status up for grabs, plus lots of models to copy like Adam Grant and Simon Sinek. I quickly realized I was not wired for it. Clear ways to make money, sure, but I couldn’t see myself giving a talk to Accenture, telling people how to adapt to The Future of Work™.

Instead, I accidentally focused on finding a mode: finding projects and kinds of work that I actually enjoyed.

Within a couple of years of doing things on my own terms, most of which didn’t have any clear path to financial payoffs: oh, I can keep doing these things for a long time!

I realized this was quite a strong tailwind I could ride for years.

The advantage of finding a mode, and sometimes “wasting” years trying to inhabit and embody this mode, is that you can later insert yourself into a niche world and know why you are doing something and on what terms.

If someone wants to hire me to give a $25k opening speech for Simon Sinek at the Accenture ITCorps AI APAC offsite, I’d be happy to do it, knowing I could playfully embrace the role of LinkedIn thought leader guy, have fun with it, and not be subject to the constraints of being that person for the next ten years.

People who embrace finding a mode early in their lives or a reinvention journey are also confusing to observe. They flow from project to project or interest to interest with much more ease than people expect. They write a book, then launch an app, then do a course, and then take a mini-sabbatical. is a good example of embracing this. Every time I hear from him, he’s launching something new, but it sort of makes sense. He’s built a life around literally just being himself.

The hidden trap of “find a niche” is not that it doesn’t work.

It’s that it will work, and you will waste years of your life on the wrong path, doing things you don’t actually want to be doing.

Finding a niche is an intellectual stance toward life. It is about figuring out what you need to achieve certain outcomes.

You need to know what niches are, how they form, and how they lead to very different financial realities. For example, if you love writing about finance, you will make a lot more money than if you love writing about buttons, or even work.

Finding a mode says, “okay I see how the world works. I see the niches. I am aware of them. I might make some changes in terms of how I communicate my thing to adapt to that a little. But at the end of the day, I’m going to keep making choices such that I have more opportunities to keep making decisions as a person that I don’t need to pretend to be.”

Third, how much and when do we actually work?

Most of us know that work days are Monday through Friday, and when many people become self-employed, they go through a phase of still showing up Monday through Friday and performing a normal workweek.

I urge people, however, to remember to fire the “manager in their head” and take the next Tuesday off. Most people would benefit from a lot more experimentation and asking some questions that help you zoom out:

• What is the ideal work month?

• What is the ideal work year?

• What are the months or years of work that I now have trouble remembering?

• What would my year look like if I had to work in four seasons?

• What are the work projects that seem more satisfying to reflect on, the more time passes?

• What is your ideal work decade?

A good way to think about spending your time is this 2x2 of life quality and mindset:

This gives us four ways we can approach a project:

• Grinding: Working as hard as possible on everything

• Small bets: Doing a bunch of small experiments while eliminating risk

• Sprints: Intensive building for weeks or months that are followed by periods of rest

• Long-game: Work you are designing your life around that you know you won’t quit because it’s so important. You find the right pace that works for your life

Over time, as people get smarter about what they want to work on, they focus more and more on their “good work” over a long game and more strategic bets that they can sink a bunch of time into over periods of weeks or months. But they also probably do different kinds of work in each of these quadrants.

Over time, many people shift to shifting between consistent effort on things they enjoy doing and short-term sprints that might be the key to getting things done or shifting momentum. For my recent hardcover launch, I’m in “sprint mode” sharing the book and promoting it. In this mode, I have a lot more energy for a lot of things like writing this Substack and tweeting. But it’s not quite sustainable as I’m not building in enough time for exploratory work, time in leisure, and at the gym. At the beginning of the year, I’ll anchor back into long-game mode around slow “most days” writing.

The key with this right-hand side is that it is moving in the direction of doing things that you actually want to do. You aren’t pivoting to a crypto ICO because it will make a bunch of money, but force you to repair reputational damage. You are making bets on your future self and interest and on where you hope you might evolve to in the kinds of work you want to keep doing. As always, this is hard to aim at, but the thing that does become more obvious over time is what not to work on.

The sprints are a way of ramping up the intensity of things you are already doing, but in some new way. It’s a way of testing new hypotheses, new kinds of work or products, or new ways of showing up in the world. It could be something like “I’m going to experiment with consistently posting on Instagram,” to “I’m going to host an event at my house in two weeks,” to “I’m going to go home early every day and hang out with my kids.”

I’m doing a “sprint” around my hardcover launch to test the viability of selling books directly right now. I’m chatting with people buying the book, doing podcasts, writing about the experiment, and reflecting on my feelings about the project. It seems promising, and it’s changing a lot about how I think about the next couple of years of how I share and sell my work. But I’m also going to slow down a bit and approach it more deliberately in the new year.

The sprint compresses time, a variable you should always be playing with. Sometimes it’s best to do nothing and go slow, waiting to see what might emerge as if you are a big game hunter. Other times, it’s worth going a little faster, executing on clear opportunities or pathways to different futures.

How to balance all of this

The best framework I’ve seen for bringing this all together is ’s “choose 2” triangle framework in his must-read indie classic Art of Gig.

On an indie path, he says that you must pick two of three and face the consequences of your decision:

1. Autonomy of Goals

2. Integrity of Methods

3. Standard of Living

I like the triangle framework because it forces hard trade-offs. If you choose to optimize for how you work and what you do, you’re likely going to face financial challenges.

This is mostly the side of the triangle I like hanging out in.

But not always!

The hack, as he says, is to make different tradeoffs for different situations:

if you want to stay in the gig economy, you can hack the triangle! Yes, you have to pick two of three, but you don’t have to make the same choices in all situations and at all times. You can rotate through them in various creative ways! This creates a much more unstable lifestyle, but it allows you to address the root causes of the pathologies that lie in wait down each pure path. It’s like keeping a set of spinning plates spinning by darting among them.

The three ways he suggests to do this are:

• Have multiple parallel gigs with different trade-offs in each: I have a lot of things I’m usually working on at once and am usually making slightly different trade-offs in all of them.

• Make different choices in different seasons: This is mostly what I do, shifting focus to my consulting training workshops whenever I need money and then going into unhinged artist mode after

• Made different trade-offs in different elements of the projects: For example, you might be willing to make compromises on how your book is packaged or sold, but not on how it is written or structured. For this substack, I take the writing much less seriously than I do my book projects, as another example.

I think this is a good summary matrix as it gets to the point that is behind almost all action in the world: it’s all tradeoffs all the way down.

The most interesting work, however, is often on the other side of rejecting the standard trade-offs that most people see as reasonable and finding the ones that may be unreasonable for others but are fun for you to make and keep making.

Ultimately, I don’t know much about “wise agency.” I’m still not quite sure what it is. But I have learned quite a bit about what I want to do, what I don’t want to do, and expect to continue learning quite a bit about it for years.

I hope I can look back on this little series in a few years and laugh because I have become quite a bit wiser.

Heyo, you made it all the way down here

I’ve been doing some form of public writing since 2015. I’ve somehow figured out how to hack a living doing things like writing books and launching premium art editions of my book. If you like what you read here, you’ll probably enjoy my books The Pathless Path and Good Work:

If you’d like to join a virtual community of others on “pathless paths” from around the world, and get access to courses, tools, and other resources I’ve created over the years, you can join The Pathless Path Community. Our recent WhatsApp community is very active if you like hanging out on messaging apps instead of Circle.

Some things I endorse:

• Readwise is offering 2 months free (I use it for book notes and reviewing highlights). Or two months free on

• Readwise Reader, which I use for RSS reading and epub reading

• Crowdhealth, an alternative to US health insurance that I’m still using while abroad

• Postbridge: A social scheduling app created by a reader without crazy upcharges for more accounts

• Kindred, a home-sharing app

• Collective for handling your S-Corp accounting needs, and Nat Eliason’s Build Your Own AI Apps course

If you received this and find yourself in a state of outrage, thinking, “What is this?” I strongly encourage you to unsubscribe below. It is your god given right, and there is plenty of other good stuff online.

A reminder: I don’t check unsubscribe alerts and never look at my subscriber list. So if you feel like unsubscribing, you can do so below.

If you missed it, I put out Part 1 of this Wise Agency series yesterday. Catch up here:

This is part of the Wise Agency series. Click here for all three parts.

On Wise Agency, Part 2

Ok, in the last post we left off in the lower right quadrant of this remix of ’s idea of the agency 2x2:

You’ve grappled with your “reality tunnels,” decided to step off the default path, avoided the ditch of negative imitation, and are ready to get lost.

Onward.

Phase 3: Surrender & Get Lost

A strong belief I have from talking to several hundred people over the last decade about work: I believe the continuously-employed adult life is unnatural.

I suspect that the vast majority of people would benefit from occasional short- and long-term breaks from their work lives, and more importantly, their work identities.

This is not to say people should follow my path and go full pathless, become self-employed or an entrepreneur permanently. But I do think most people working today would benefit from elevating the importance of looking for time and space in their lives to get lost, embarking on season of solitude, wandering, or adventure.

But even if you pull off such a feat, it’s still hard to surrender fully to such a phase.

After quitting my job, I reflexively rejected many of the the replacement identities on offer: venture-backed founder, tech worker, impressive freelancer, “thought leader.” This is the trap of phase two I talked about yesterday.

In my mode of rejection, I still had the feeling like I should be doing something.

This tension nagged at me for nearly a year as I floundered around the US for about 15 months taking freelance gigs, booking random trips, and flaneuring around Boston.

Then, I booked a one way flight to Taiwan. Perhaps it was a seed inside of me from my future nudging me in this direction or just my acknowledgement that wandering around the US begging my full-time employed friends to hang out with me during the day. It doesn’t really matter. But arriving in Taiwan was enough of an environment shift that I finally gave myself permission to not have a plan.

It was time to wander in the metaphorical wilderness of my new path.

I shifted from trying to do things to trying to do nothing at all.

Which was confusing.

I had this inner exuberance about shifting in this new direction but also felt immensely stuck. I’ve never accomplished or done so little.

I was in what in his recent book, Conscious Accomplishment, calls this “inner purgatory”:

Inner purgatory is the intermediate state between focusing on your inner work and feeling invigorated to take creative action in the world. When you’re in inner purgatory, you desire to accomplish things from an updated perspective, but find it inexplicably difficult. You may struggle with a lack of motivation, inspiration, or energy for external goals, despite knowing that you want more for your life than doing inner work all the time.

Activities that once came easily may feel difficult. You may no longer feel like you have the same raw horsepower you once did. You can try to will yourself to push through things, but without the natural force behind you, you eventually exhaust yourself.

Underneath it all, I was rewiring myself. I was letting go of my past anxiety-driven achievement patterns and toward ones that were more natural and driven by self-awareness. But this didn’t just happen. It was a process.

I needed to let go and mourn the loss of my inner grinder, as I wrote about in Good Work:

Letting go of a life strategy that seems to be working can be terrifying. For me, it meant stepping away from a formula for life that provided me with money, status, and real confidence. I loved feeling competent and being good at what I did. So realizing that I never wanted to return to that world initially filled me with grief. I do miss telling people about my impressive achievements and watching their eyes light up with instant respect.

This period was tough.

I was scared to tell people close to me what I was doing, or really what I wasn’t doing. I lied. I made up fake plans. But I could see that the instant respect I used to command was gone. I still craved respect and hadn’t fully sat with the insecurity of not having that anymore. Comments from other hurt.

What is your plan?!

There is none. I felt lost. Intensely lost.

But like I said, underneath, I also had this deep sense of okayness. I knew I was on the right metaphorical path even if I couldn’t “prove” it. I’ve quoted Rebecca Solnit on this so many times because when I read this line in her book The Field Guide to Getting Lost during this period, it send a jolt through my body:

That thing the nature of which is totally unknown to you is usually what you need to find, and finding it is a matter of getting lost

Getting lost is beautiful.

But this phase can be a trap too!

If you spend too much time being lost, distancing yourself from the default world, things can quickly turn into escapism.

Just like its easy to quickly embrace a new path after quitting your job, its just as easy to immerse yourself into groups where being lost is a permanent lifestyle.

• Spiritual paths to enlightenment

• Productivity & personal growth toward endless achievement

• Seasons of “healing” and therapy and inner work that never end

• Psychedelic and reality altering substances or communal practices

• Going to Bali and not being able to live “back” where you left behind

The key with these things is to embrace them to leave them.

• Go to Bali to eventually be able to leave metaphorical Bali (I did this for two months in 2019, it was a perfect place to hang out 1.5 years into my journey). You can even stay in Bali but you don’t want to live in the reality of Bali

• Embrace the productivity hacks to leave the productivity hacks

• Do the psychedelics and healing work to be able to leave the healing work behind

You’ll also be tempted to join the mob against the world you left behind.

The way out of this phase is to realize that no escape is possible.

You have the desire to be saved but you should stop trying to be saved. You must finally accept that you need to navigate uncertainty, doubt, and vulnerability and befriend them instead of running from them.

For me, Joe Hudson’s work has helped me understand the rough process I took to get out of this: befriending them.

Before this, I spent 10+ years in what Joe calls the golden algorithm: Run from emotions only to re-create them from my action. My formula was simple: Try to escape my current situation => run from emotions => search for another job => praise and validation => feel same dissatisfaction again => repeat.

The way out was simple but hard: feel the emotions. Fully.

Getting lost and making your way out is about accepting it all:

• The uncomfortable emotions

• How you may not be a fit for the default world anymore

• Your frustration at how things work

• The many new challenges you are facing

• How others aren’t open to your new perspectives.

And saying, ahhhh yes, this is okay, let’s keep going.

In other words, you can leave the world but you must leave the world in order to find it again. You can leave work temporarily, only to find it again in new form.

Phase 4: Wise Agency

It’s exciting to think you can arrive at the magical upper right quadrant, the place Peter called “agentic sage,” in his first post.

I think the only realistic way to arrive there is to completely lose interest in any such arrival.

The key idea that I picked up in my season of solitude was that only through knowing thyself can one figure out what is worth doing.

This inverts the logic that we do what others around us are doing or that we should do what is “smart” or best practice. But when you approach life in this way, you can end up making interesting choices, ones only you can make. This looks like “agency” to others but weirdly will not feel like you are doing much at all.

One frame that’s helped me think about knowing thyself is John Vervake’s “four ways of knowing” or the 4Ps:

• Propositional (facts, concepts)

• Perspectival (other peoples ideas, other viewpoints)

• Procedural (how to do things, process)

• Participatory (active engagement with)

Early in our lives, most of us over-index in the propositional (“I know these facts”) or the procedural (“this is the correct way to do things!”).

A movement toward wise agency requires embracing all four and then continuing to engage in these throughout life, ideally moving away from the propositional and procedural as you learn more about yourself and the world.

As you enter a new phase, you inevitably engage in new modes. For me, some of the ways I engaged were:

• Perspectival: Travel to understand new ways of living and opportunities; podcasts to understand new perspectives

• Procedural: Books to understanding how to approach new problems; courses to understand how things really work

• Propositional: Learn basics like tax law, accounting rules, and realities of making money on my own so you can ensure you stay in the game

These give you confidence about your new path and enable you to see new possibilities for your life that you didn’ see before.

But the trap is that you lean too hard on the ones you are best at: The engineer who leaves their job spending all their time on reading how-to books and prodctivity hacks and only spending time trying to make money in the new startup, who forgets to take a day off to assess what might have changed after shifting in this new direction.

This is why the last one and most overlooked is Participatory knowing: through action I can come to know more about myself and the world.

This can be a broad definition of participation:

• Offering something: supporting family members, mentoring people, giving encouragement, sharing your expertise, being the person who reaches out

• Hosting and gathering: dinner parties, book clubs, online communities, group chats with intention, workshops, retreats, or even just a group chat

• Doing new things: taking a class, volunteering, joining a sports league, learning an instrument, showing up to local government meetings, traveling somewhere that challenges you

• Creating something: a business, a piece of writing, a podcast, art, a newsletter, open-source software, a course, even a journal entry

• Religious or spiritual practices: Religious groups, Meditation, mindfulness, breathwork, retreats, and the endless list of woo- and woo-adjacent practices

This kind of participation in the world is increasingly important the further you are away from any sort of default path you left behind.

Vervaeke argues that the modern human needs an “ecology of practices” to stay sane. For me writing has been a powerful practice but so have things like meditation, breaks from work, time with my daughter, breathwork, travel, and all of the weird work things I do in public that stir up all sorts of emotions and discomfort.

On a podcast, he said the aim of these participatory practices if to be open to failure:

An ecology of practice is a complex dynamical system. It takes a time and effort and commitment and a willingness to transform and fail and learn from mistakes in order to make this work.

This rhymes with Peter’s frame of being “less foolish” rather than seeing “wise agency” as a place for arrival.

A metaphor I offer for this is Posting:

Posting is not just about posting online but it can be that too. It is about making an offering to the world. It is moving in the direction of things that feel scary but feel right. It can be any form of participatory action. It is ultimately about making an “opening offer” to the world and being okay that nothing may come back while also being open to whatever may come to you regardless.

At it’s core, “posting” is a generous act, and it is a multi-player game.

I think this is an important metaphor because so many people have reflexively rejected the digital age. Cal Newport tells us to run from the internet, hide in your cavern and do your deep work. I think in today’s age this is the wrong stance.

Real growth comes from engagement. Dancing in the chaos of the world as it is and being open to seeing where you might be able to take wise action.

The biggest challenge for most people is that wise action is very hard.

This is because many of the things you learned about how to operate in that first chapter of your life will no longer be effective.

Either because you are not operating with the same source of fuel (things like the desire to prove others wrong), or that the rules of the world you are now inhabiting and participating in are different.

But now, you have some sense of what you are capable of and more importantly, not capable of. Having this wisdom enables you to hold everything you do much more lightly. Success isn’t your savior and you don’t attach yourself to script of being special through work. This opens you up to the ability to be immensely existed by what others around you are doing. You are amazed at how little you are threatened or triggered by their accomplishments. You don’t feel as much pressure from your projection of “the world” about what you should be doing.

Despite this, you will be constantly tempted to take shortcuts. You will be shown quick paths to riches, easy ways to sell out what matters, and hacks that will enable you to do things the easy way. You will be offered instant acceptance in new groups that promise belonging and a refuge from the world. This never ends.

But wise action is knowing that all of these things are paths to foolishness.

Wise agency is about knowing that the path forward in the world is usually just about surrendering to the work and ways of life that become more obvious over time, through simply continuing to show up in the world.

It may seem like you are arriving when you realize all of this. That you are smart.

But you are wise enough to know that you are still on the beautiful journey of life.

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I recently launched my premium hardcover version of The Pathless Path. If you order before Christmas, I’m shipping it out gift wrapped (custom note optional) with a bonus notebook and note cards.

check it out

This is part of the Wise Agency series. Click here for all three parts.

I gave a talk for ’s Stoa last week around the idea of “wise agency.” It was a fun topic to think through.

Agency is an idea I’m partial to, and I wrote about it in The Pathless Path in the context of Fromm’s idea of “positive freedom.” Positive freedom, in my interpretation, is about leaning fully into your own genuine path and the things that you actually want to be doing, in a sustainable, life-giving way. Agency was the mode of practicing such freedom through experimentation, spontaneity, and discernment about what a good life looks like for you.

In the past couple of years, however, “agency” has become a meme in itself. It’s a suitcase word that can describe anything from ironically ordering 153 chicken nuggets at 2 am to celebrating one’s preferred authoritarian leaders crushing their opponents.

At its best, it is used to describe people moving on a positive trajectory in their lives. We can call this “wise agency.” And at its worst, it’s a cynical or nihilistic embrace of do whatever you must do to achieve your desired ends, regardless of the fallout. Or simply, foolish agency.

Sadly, I see this cynical stance everywhere. From the widespread embrace of gambling and speculative trading to the loss of interest in committing to work without immediate payoffs (or asymmetric equity payoffs) to the embrace of sketchy tactics to make money online, we appear to be going through a period where we have more agency than ever but seem not to have any idea what to do with it.

This has all made me a bit tentative to write much about agency. After all, how foolish must I be to think I have any of this figured out?

After my initial rejection of his offer, Peter pushed me to do it, and I’m glad I did. I’m not sure I have anything novel to offer here, but I do have a better understanding of what I’m trying to do in my own life.

This post got a bit out of hand, so I’m sharing part 1 here. Part 2 will follow…sometimes in the future.

The Problem With “High Agency”

For this talk, I’m building upon Peter’s ideas in a great piece titled, How To Win Friends and Get Things Done…With Wisdom. In it, he argued a similar notion, that “Highly intelligent people with high agency can win many ‘friends’ and get a lot of things done, but they might be doing so foolishly.”

He came up with the following 2x2, which immediately became its own meme, as added a simple red line, showing his journey.

As Peter responded:

Exactly!

It maps to my personal journey.

• NPC. You don’t take the “blue pill”; you’re born into it.

• Agentic fool. Unexamined success = unquestioned “good.” Hustle, hustle, hustle until burnout.

• Spiritual bypasser. A spiritual emergency happens. Aliveness. A new way of being opens up. You overindex on it. It becomes impotent.

I’ve experienced a number of these phases too.

I’ll attempt to map my experience and add my spin to it.

Phase 1: World-Class Hoop Jumping

This was me at 32:

• Working for CEOs & Boards of the biggest companies in the world

• Knew how to “hack” the career game, networking my way to new jobs, and how to break into top-tier institutions

• Guaranteed career path for even more $$, success & status

• Living in New York City

I knew how to play the career game. I felt agentic, or at least if I heard the phrase “you can just do things,” I would have thought I was doing it. Friends would come to me and ask for help, and I felt like I had some secret knowledge of how the world worked because when they followed what I said, it often worked.

But I was a fool.

• I didn’t stay in a job for more than 17 months for eight years

• Constantly wanted to escape my present to an imagined future

I couldn’t see the frame, and even though I’d poke at the edges, I kept moving forward playing the same game.

I was stuck in a cycle of insecure agency.

My “moves” from my early twenties that did improve my situation were no longer useful. They were keeping me in this vicious cycle: I needed to keep moving to avoid what was really bubbling under the surface.

The thing that tipped the scales for me was a growing disconnect between my intense desire to learn and explore my curiosity and the scoreboard (my income).

Eventually, I got to the point where the costs of this diminishing intellectual curiosity were no longer worth it.

But how do you start to see these unconscious scripts you are following?

I personally love Robert Anton Wilson’s frame of “reality tunnels.” These help us make sense of “the muddle of existential reality or ordinary experience,” and the more we are hypnotized by them, the more our “existential experience we then edit out or blot out or blur into conformity.”

One thing I’ve realized is that many people will say things like “oh, society is forcing us all to do X.” But after asking hundreds of people the scripts and stories they grew up with, I found something much more interesting.

1. Most people may have more beliefs and unconscious scripts than they think

2. Our strongest reactions to others’ scripts and our own indicate our most interesting avenues of exploration

In workshops, I’ve been asking people to go through 15 sets of statements and to give themselves a +1 if they have an extremely strong negative or positive reaction.

You can do it too. Go through these and +1 if you react strongly

• “I must consistently improve to be a good person”

• “Anything worthwhile requires suffering”

• “Work hard, and you’ll be rewarded”

• “You should always do the hardest thing possible in your life.”

• “Get good grades, get to a good university, and you can then do anything you want.”

• “You don’t have to enjoy your work. Work is just to pay the bills.”

• ”You should love what you do. Work is the most important thing in the world.”

• “Anyone not doing inner work is sleepwalking through life.”

• “Playing society’s default game is a sucker’s move.”

• “The contemplative life is the best life.”

• “Rich people are worse people”

• “Money is just a flow of energy”

• “Don’t be a sucker, everyone is trying to get rich”

• “My spiritual journey is the most important journey”

• “A pathless path is fundamentally lazy”

Feel free to put your score or reactions in the comments.

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But the key reflection here is that, “wow, I have more going on than I thought.”

Many people often follow this thread and eventually decide:

It’s time to blow it up.

Phase 2: Blow it up

Blowing up your life is underrated. Reading Life is In The Transitions made me realize that our lives are already being blown up all the time, so better to lean into it.

Like Peter’s initial diagram, this is often a period for easily falling into the traps of becoming an agentic fool. You’ve thrown off the shackles of your own reality tunnel and are now SMART. You know the game you were playing and exited.

But as soon as you start walking in a new direction, you see traps around you.

The fundamental challenge is leaving behind your previous path without identifying with the rejection.

In other words, reject the default path, but don’t turn rejecting the default path into your personality.

But this is incredibly hard!

In today’s world, there are an endless number of people who understand that they can turn the vulnerability of not knowing what’s next into profit.

We are often tempted by two forces:

Comfort in conformity, as Jed McKenna warns: “The first thing we want to do when we begin our journey is find the companionship and validity that comes with an established group, and in so doing we effectively end the journey before it begins.”

The desire to “find the others” is vital. You do need people to support you on a new path. But if we mistake belonging for arrival, we risk getting stuck before we get started.

The second trap is trading one identity for another. As Rene Girard wrote: “Modern society is no longer anything but a negative imitation and the effort to leave the beaten paths forces everyone inevitably into the same ditch.”

Which is hard because of how many legible replacement suits are offered to us immediately upon leaving the default path:

The whole game of this phase is to avoid the ditch.

But I think avoiding the ditch for most people is impossible.

I went through a phase when I was pretty angry at my previous path. Why are the organizations led by all these people who love manipulating people? Why are they promoting the most political, not the most valuable? The system was broken, and early on, I wrote many essays trying to make my case!

Eventually, I saw it was a trap. Although there’s lots of money to be made selling coaching or products to people who want to escape, I saw it was not going to be “wise action” for me. I’d end up attracting people I didn’t want to help, and I’d be spending my time with similarly frustrated people. I knew I needed to process this frustration, accept it, and move on.

I think most people will spend at least some time in the ditch. The key is to know that this phase exists and resist all attempts to make it your identity.

The key to moving past this? Allow yourself to get lost.

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Heyo, you made it all the way down here

I’ve been doing some form of public writing since 2015. I’ve somehow figured out how to hack a living doing things like writing books and launching premium art editions of my book. If you like what you read here, you’ll probably enjoy my books The Pathless Path and Good Work:

If you’d like to join a virtual community of others on “pathless paths” from around the world, and get access to courses, tools, and other resources I’ve created over the years, you can join The Pathless Path Community. Our recent WhatsApp community is very active if you like hanging out on messaging apps instead of Circle.

Some things I endorse:

• Readwise is offering 2 months free (I use it for book notes and reviewing highlights). Or two months free on

• Readwise Reader, which I use for RSS reading and epub reading

• Crowdhealth, an alternative to US health insurance that I’m still using while abroad

• Postbridge: A social scheduling app created by a reader without crazy upcharges for more accounts

• Kindred, a home-sharing app

• Collective for handling your S-Corp accounting needs, and Nat Eliason’s Build Your Own AI Apps course

If you received this and find yourself in a state of outrage, thinking, “What is this?” I strongly encourage you to unsubscribe below. It is your god given right, and there is plenty of other good stuff online.

A reminder: I don’t check unsubscribe alerts and never look at my subscriber list. So if you feel like unsubscribing, you can do so below.

On Monday or Tuesday, we’ll be receiving the notebooks so the team I’m working with at Otterpine can immediately start shipping the hardcover bundles people have ordered.

I decided it would also be fun to gift some of the notebooks for Black Friday. The only thing you need to do is pay shipping (US Only).

You can grab one here (discount automatically applies at checkout).

One issue: We can only do this in the US right now. We still have some work to do to set these up for international shipping.

Grab The Notebook

Also, I’m including all the digital editions of my books if you buy the premium hardcover

In addition to a free notebook and note cards, which are already included, if you purchase the launch bundle before Christmas, I’ll throw in digital versions of both of my books:

• PDF, EPUB, and Kindle Versions of The Pathless Path

• Audible code (while they last) and/or Podcast link to The Pathless Path Audiobook

• PDF, EPUB, and Kindle Versions of Good Work

• Spotify Gift code for Good Work (while it lasts) and/or Podcast link to the Audiobook

• And the PDF of the premium version itself.

Buy The Premium Hardcover - $95

I need to set this up on the backend but if you just email me your receipt this weekend, I’ll hook you up (also obviously good for previous purchases too).

Why am I doing this?

Bundles: The thinking behind a higher-priced book is that it helps reach the people who want all this stuff. Price discrimination: either you might want to support my journey, or you are just the kind of reader who buys 5 different versions of a book anyway.

Giving Stuff Away: It’s fun, and it’s always been part of how I do things. I started experimenting with alternative gift economy approaches in 2018.

Why Not?: I’ve been trying to lean much more into “what is the most generous thing I can do?” and “what is the most fun thing to do here?” Expect many more experiments along these lines in the future (and ideas welcome!).

21 “Pathless” Book Recommendations

I recently updated my “recommended reads” site for people on unconventional paths:

See Recommended Reads

That’s all for this week. I’m likely going to be dropping a few longer essays I’ve been working on for the holidays. Stay tuned!

-Paul

• I’m participating in this wise agency multi-part workshop with . It’s offered on a gift pricing basis, and you can learn more here.

• is hosting a multi-city “internet serendipity” tour. Pathless people will be at many locations, including Boston, DC, Austin, Seattle, Vancouver, SF, Denver, Miami, and Columbus: Register here

• I’m judging a writing competition with the . Here’s the prompt: Write about a moment when you (or a character) stepped off the expected road, or dreamed of doing so. What happened when you stopped following the map? Lots of cool prizes included, including a copy of my hardcover: see details here.

When Paperbacks Were Too Sketchy For Publishers

In the 1950s, paperbacks were not considered serious works of art by publishers and even some authors. Using cheaper paper and appealing to “lowbrow” mass audiences, paperbacks were the bottom rung of the literary hierarchy. Trade publishers were initially leery of paperback publication, “fearing it would cheapen authors’ reputations and cut revenues.” In a conversation I had with Eric Jorgenson, diving into the weird history of publishing, we both took a peek at what some of these “lurid” covers looked like:

Also, it wasn’t just publishers. Many authors also didn’t want their books “between the lurid paperback covers in favor of the 1940s and 1950s.” Some hardcover houses went so far as to include “the right to approve paperback covers in their reprint contracts.”1

Despite this, consumer preferences were undeterred. In 1947, approximately 95 million mass-market paperbacks were sold for slightly more than $14 million, but five years later, 270 million copies were sold for $40 million. By 1959, nearly 286 million copies were sold for $67 million, and “dollar sales of paperbacks exceeded those of hardcover trade books for the first time, even though paperbacks were much cheaper than hardcover books.”2

But the stance of seeing the hardcover as the only “real” book persisted, which basically meant less money for publishers and a bigger upside for authors. While his novel, Carrie, was purchased in hardcover for $2,500 in 1973, Stephen King’s writing journey really took off when he sold the paperback rights, one year later, for $400,000, to a completely different publisher.

This pattern repeats throughout history

In my research into the publishing industry, this pattern repeats throughout history:

1. Publishers look down on new formats (see paperback, ebook, audiobook, translation, and even merchandising rights)

2. Authors embrace them independently, profiting from them, or authors find ways to retain and sell rights after already having a successful book

3. Publishers eventually move to own and restrict more of these rights

If you want to publish a book through the traditional route, it is nearly impossible to avoid giving up these rights as an entire basket without investing in the book yourself or through a hybrid publisher.

Increasingly, however, this doesn’t make sense for the author nor the publishing house.

For the author, it’s clear why it doesn’t make sense. The authors care about being a viable creative person and making money from their work in any way possible. The publisher is not in the best position to actually execute on this. The publisher is great at packaging a book and selling it via traditional distribution channels. But even after 10+ years with ebooks and audiobooks, they appear to have no interest in doing anything creative with these formats or even pricing them competitively, let alone unleashing authors to make money using the IP and content despite many being world-class creative humans!

For a publisher, I think this is a weird self-own, too. In the age of the internet, a book is a meme, and the publisher should be interested in helping the meme spread as much as possible. But many publishers make it incredibly hard for authors to share their work. Unless the authors commission the cover or illustrations themselves, authors often are not legally able to take pictures of pages, pictures, images, or anything related to the book. They cannot remix the content, do interesting bundling deals, discount the ebooks and audiobooks over extended time periods, create interesting merch, or create alternative or high-end collectible editions of the book, like I did with The Pathless Path.

If I had sold the rights to my work, I never would have been able to create this:

a button to take you to the order page

This is a silly creative tax on our best writers

More than that, I likely never would have even thought about doing such a thing because as soon as I signed away all my rights, I would no longer be the creative director of my own work and likely would have lost motivation to come up with any ideas. This is a hidden creative tax on the most impressive writers of our generation.

The Pathless Path is clearly “working,” and as I interact with readers, I’m in a virtuous cycle of learning and playing with better ways of sharing and packaging my work. At scale, publishers have distribution advantages, but indie types can outcompete them with speed and experimentation. While these old companies still rely on the one, big, beautiful launch, I’ll be out here trying stuff, launching, relaunching, and having fun along the way, not needing to worry about the business case for any single decisions.

AI will expand the possibilities and real options of creators just like every technology has throughout history. Just this week, Amazon enabled AI-assisted English-to-Spanish translation. I already have some interesting AI-generated custom printed editions in the works for readers that I’ll share in 2026. With such cutting-edge technology moving so fast, I am excited to be in a similar position to King and others, retaining rights to capitalize on the upside of progress without needing to wait for a committee at a random company to decide that it makes sense.

I suspect this is why self-publishing, at least in the non-fiction tech/productivity circles I hang out with, appears to have hit a tipping point.

Self-publishing is having a moment in non-fiction

Interestingly, as I reflected on my reading habits, 90% of the non-fiction books I’ve finished (I’ve started many others) have been written by people who self-published. This happened without me being aware until I took stock last week.

While many popular non-fiction books are increasingly predictable, these books were weird, interesting, unpolished (in a good way), and thought-provoking.

Every time I write about this stuff, I get tons of messages from authors. This week, shared a reflection on his experience with publishing.

His story captures his own disillusionment with the industry, which started almost immediately after signing his book deal, Losing the Nobel Prize. He makes a trip to New York City to visit his editor at W.W. Norton. As he makes his way through the building, he finds that his editor’s office “was, in fact, the janitor’s closet. Broom, mop, cleaning supplies, and all.”

Early on, he faced pushback on his decisions. He had to fight for the title, eventually winning. But the publisher won, choosing their own image they preferred for the cover. In a weird twist, the publisher bought the rights from someone who didn’t own them and had to redo the cover. But Brian shares: “Embedded in my contract was a clause I’d barely noticed. Any new edition—paperback, audiobook, revised hardcover—required a new launch, new publicity, and a new book tour.” It forced a 2nd release, and the hype from the new launch enabled the book to take off.

What would have happened if they had never made the mistake? Would people have forgotten about it? Would Brian have stopped talking about it?

He pondered these same questions and had an awakening: “I used to walk past those grand Mad Men-appointed publisher lobbies and feel envy. Now I see them for what they are: monuments to a past that no longer exists.” He decided to self-publish his next three books and concluded, “The institutions you revere are more fragile, more arbitrary, and more human than you think.3

When I step back, I think this sort of waking up is happening to many more people working in creative fields, especially those who started doing their work online, and even more so for younger people who may not have inherited the scripts from the “old world.”

We need new plumbing to enable creatives

, founder of a very internet-first company, Kickstarter, has been doing some interesting work in this vein with his attempts to get an “Artist’s Corporation” (A-Corp) established in the US. It would be a legal vehicle for creators that would enable outside investment, payments, revenue-sharing, and even non-profit donations. His work on this made me realize so much of what we see as possible is downstream of the legal and financial plumbing of the economy.

Change the protocol layer, and you can shift the imagination of the participants of the system.

In a recent podcast with NPR discussing the idea, he pointed to the absurd status quo: “Artists are service providers who create assets that these larger enterprises acquire and capitalize on.”

With the internet, you no longer need to create raw material for bigger companies. You should own your own creations.

And do fun stuff like this.

P.S. The hardcover bundles are on track to ship by early December; we are only waiting on a container ship that’s carrying the notebooks, which is currently in the middle of the Atlantic. If you purchase the Medici tier, I’ll send you daily updates.

Here are some reviews from friends I’ve shared it with so far.

But first, a quick hardcover update

Sales of the new hardcover are going well.

We’ve pre-sold about 175 books to 20 countries now. Sharing the flags here because it’s kind of wild to see so much support from around the world!

🇺🇸 🇬🇧 🇨🇦 🇸🇬 🇹🇼 🇸🇰 🇷🇸 🇵🇹 🇳🇿 🇲🇺 🇯🇵 🇮🇱 🇮🇪 🇭🇰 🇩🇪 🇨🇭 🇧🇪 🇦🇺 🇸🇪 🇰🇷

And we’ve started shipping out some of the early copies to people who purchased the Medici tier, as well as people helping me promote the book.

The rest of the hardcovers are in port in NY, and the notebooks are en route from Morocco right now. Barring any logistics issues or global pandemics, we should be able to get these to people before Christmas (we can gift wrap and customize these with notecards, just add it in the comments of the cart).

I also shared an unboxing video this week:

If you’d like to check the book out or want to share it, check it out here.

Grab the book

Onward

#1 The appropriate amount of effort is zero

I love this essay from - it’s a simple but powerful idea:

There is an appropriate amount of energy required for each activity. Holding a cup, turning a steering wheel, or writing a blog post all need exactly the amount of energy that they need. This may sound like a truism, but if it were so obvious, why do many drivers often realise they are driving with a vice-like grip, with tension running up into their shoulders and jaws?

Let me share my slightly unusual definition of “effort”: it’s the felt experience of expending energy beyond what an activity requires, like tensing your brow when you try to understand something, or the excess tension in your hand when you hold your phone^.

Using this definition, it’s clear that the appropriate amount of effort for any activity is zero.

This doesn’t match with many of the stories we have about work and what’s worth doing, but if we accept this definition, where can you try less?

Read the full essay.

#2 You are not broken

had a great video essay on the aggressive hacks people employ in the self-help and creators worlds to hack attention.

In the video, he also highlights the pressure on creators to avoid anything even partially critical of other creators, especially those with large followings. This transforms the creative landscape from a space of healthy intellectual debate into one of transactional relationships, where people are always looking to “trade up” favors to people with bigger and bigger followings. This pressure is part of the reason I’ve scaled back my podcast and mostly focus on interviewing people I’m genuinely curious about.

This tension is a challenge, though, because it’s beneficial to befriend anyone who can amplify your work. If Oprah offers to cross-promote with me, I’d likely do it. Over the past couple of years, I’ve purposefully avoided this kind of favor trading with people whose work I don’t enjoy or tactics I don’t respect. Over the long term, I think this isa good approach because it means I’m sharing things I genuinely like and collaborating with people that inspire me.

Managing this is hard, and if you aim to have an audience for your work, you need to think about these kinds of tradeoffs. Many successful people are willing to grow at almost all costs, and so you just need to know what you are willing to do too.

One way I’ve leaned against the pressures is simply to write what I actually think. My essay on why you might not need to suffer and broader thoughts on the bad effects of hustle ideas and language have likely rubbed a few people the wrong way, people who could have otherwise “helped” me. But that’s okay because I stand behind the ideas.

Anyway, I appreciate Matt adding some thoughtful disagreement to the conversation.

#3 Jevon’s & Baumol

proposes a persuasive theory of how dual forces: rising costs from Baumol’s cost disease and abundance via Jevons’ paradox (tasks get cheaper, we consume more) combine to shape a new reality of work in the age of AI, not to mention political weirdness as our work realities evaporate:

In an interesting way, this hints at where Baumol’s will finally run out of steam - because at some point, these “last 1% employable skills” no longer become substitutable for one another. They’ll become strange vestigial limbs of career paths; in a sense. We have a ways to go until we get there, but we can anticipate some very strange economic & political alliances that could get formed in such a world.

a16z

Why AC is cheap, but AC repair is a luxury

If you live in the United States today, and you accidentally knock a hole in your wall, it’s probably cheaper to buy a flatscreen TV and stick it in front of the hole, compared to hiring a handyman to fix your drywall. (Source: Marc Andreessen.) This seems insane; why…

Read more

7 months ago · 181 likes · 25 comments · Alex Danco

#4 The housing theory of everything

This was the title of a good essay from a few years back. The takeaway was stark:

Western housing shortages do not just prevent many from ever affording their own home. They also drive inequality, climate change, low productivity growth, obesity, and even falling fertility rates.

Every young person I know, including those who have bought a home, has been talking about this for years. Among my friends, even those who were able to secure a home, there is a sense that the system isn’t quite working. On top of that, everyone sort of knows that many people are able to afford inflated prices with support from parents.

With the recent inflation and doubling down on restrictive housing policies (outside of rare places like Florida, Arizona, and Texas), this has led to some pretty wild shifts. While I’m a happy renter, I do wonder if I’d be thinking about my path differently if housing hadn’t become another speculative financial asset.

Check out the following charts I came across just in the last month.

Price-to-income is the highest it’s been in 50 years

Remote work kind of killed the retreat from cities?

Someone shared how remote work seems to have plateaued at 28%. While this is awesome and I love to see it, it’s certainly not high enough for people to be making permanent housing decisions to live in more rural areas. Most people know they have to be able to change jobs and have access to opportunities in a modern career, and knowing only 28% of jobs are remote (though this seems high?) is not enough to permanently reinvent, like so many were thinking of doing during the pandemic.

The median homebuyer was born in 1969.

Lots of people’s wealth is tied up in homes, and so it is political suicide to reimagine a different path. I suspect, however, that this cannot hold.

#5 Phone and kids

Emily Oster’s books are great for pregnancy and the first few years of parenting. She shared a nuanced but straightforward analysis of confusing data and hot takes from other parents.

She recently did a nice post on the impact of phones on kids. Here’s her takeaways:

• It’s difficult to definitively determine whether social media affects teen mental health because most of the studies we have cannot reliably show causality.

• There are tradeoffs to allowing your teen to use social media. Although the effects of social media are negative on average, there are people who benefit from it.

• Phones are a clear distraction in schools, and the evidence so far suggests that banning them improves learning.

• Regulation on social media age limits is unlikely, so it falls to parents to set boundaries. Much like teaching kids to drive, we need to decide when they’re ready for phones and guide them in using them responsibly.

#6 Books

I’m really enjoying the current reads:

• Breakneck by Dan Wang: Strong, clear, and interesting comparison between two modes of state planning, China vs. the US.

• Composing A Life: Just started, but a very good book recommended by that details four women’s different approaches for literally “composing” their lives

• Conscious Accomplishment: His new book is very good. If you’ve been someone who has gone through a work reinvention or gotten stuck on spiritual paths, this book is for you. I’m sort of blown away with how much detail Scott has managed to inject into his own journey from startup founder to someone who has a much better relationship with work and life itself. His idea of the “inner purgatory” described something I definitely went through from 2017 to 2019:

  “I call this period inner purgatory. Inner purgatory is the intermediate state between focusing on your inner work and feeling invigorated to take creative action in the world. When you’re in inner purgatory, you desire to accomplish things from an updated perspective, but find it inexplicably difficult. You may struggle with a lack of motivation, inspiration, or energy for external goals, despite knowing that you want more for your life than doing inner work all the time. Activities that once came easily may feel difficult. You may no longer feel like you have the same raw horsepower you once did. You can try to will yourself to push through things, but without the natural force behind you, you eventually exhaust yourself.”

Heyo, you made it all the way down here

I’ve been doing some form of public writing since 2015. I’ve somehow figured out how to hack a living doing things like writing books and launching premium art editions of my book. If you like what you read here, you’ll probably enjoy my books The Pathless Path and Good Work:

If you’d like to join a virtual community of others on “pathless paths” from around the world, and get access to courses, tools, and other resources I’ve created over the years, you can join The Pathless Path Community. Our recent WhatsApp community is very active if you like hanging out on messaging apps instead of Circle.

Some things I endorse:

• Readwise is offering 2 months free (I use it for book notes and reviewing highlights). Or two months free on

• Readwise Reader, which I use for RSS reading and epub reading

• Crowdhealth, an alternative to US health insurance that I’m still using while abroad

• Postbridge: A social scheduling app created by a reader without crazy upcharges for more accounts

• Kindred, a home-sharing app

• Collective for handling your S-Corp accounting needs, and Nat Eliason’s Build Your Own AI Apps course

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